diff --git a/dd-smoke-tests/apm-tracing-disabled/application/build.gradle b/dd-smoke-tests/apm-tracing-disabled/application/build.gradle
new file mode 100644
index 00000000000..3f5c868f46a
--- /dev/null
+++ b/dd-smoke-tests/apm-tracing-disabled/application/build.gradle
@@ -0,0 +1,38 @@
+plugins {
+  id 'java'
+  id 'org.springframework.boot' version '2.7.15'
+  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
+}
+
+def sharedRootDir = "$rootDir/../../../"
+def sharedConfigDirectory = "$sharedRootDir/gradle"
+rootProject.ext.sharedConfigDirectory = sharedConfigDirectory
+
+apply from: "$sharedConfigDirectory/repositories.gradle"
+
+if (hasProperty('appBuildDir')) {
+  buildDir = property('appBuildDir')
+}
+
+version = ""
+
+java {
+  sourceCompatibility = '1.8'
+}
+
+if (hasProperty('apiJar')) {
+  dependencies {
+    implementation files(property('apiJar'))
+  }
+} else {
+  dependencies {
+    implementation "com.datadoghq:dd-trace-api:+"
+  }
+}
+
+dependencies {
+  compileOnly 'com.github.spotbugs:spotbugs-annotations:4.9.8'
+  implementation 'org.springframework.boot:spring-boot-starter-web'
+  implementation group: 'io.opentracing', name: 'opentracing-api', version: '0.32.0'
+  implementation group: 'io.opentracing', name: 'opentracing-util', version: '0.32.0'
+}
diff --git a/dd-smoke-tests/apm-tracing-disabled/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/apm-tracing-disabled/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/apm-tracing-disabled/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/apm-tracing-disabled/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/apm-tracing-disabled/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/apm-tracing-disabled/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/apm-tracing-disabled/application/gradlew b/dd-smoke-tests/apm-tracing-disabled/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/apm-tracing-disabled/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/apm-tracing-disabled/application/gradlew.bat b/dd-smoke-tests/apm-tracing-disabled/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/apm-tracing-disabled/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/apm-tracing-disabled/application/settings.gradle b/dd-smoke-tests/apm-tracing-disabled/application/settings.gradle
new file mode 100644
index 00000000000..b5f9a021357
--- /dev/null
+++ b/dd-smoke-tests/apm-tracing-disabled/application/settings.gradle
@@ -0,0 +1,32 @@
+pluginManagement {
+  repositories {
+    mavenLocal()
+    if (settings.hasProperty("gradlePluginProxy")) {
+      maven {
+        url settings["gradlePluginProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    if (settings.hasProperty("mavenRepositoryProxy")) {
+      maven {
+        url settings["mavenRepositoryProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    gradlePluginPortal()
+    mavenCentral()
+  }
+}
+
+def isCI = providers.environmentVariable("CI").isPresent()
+
+if (isCI) {
+  def sharedRootDir = "$rootDir/../../../"
+  buildCache {
+    local {
+      directory = "$sharedRootDir/workspace/build-cache"
+    }
+  }
+}
+
+rootProject.name='apm-tracing-disabled-smoketest'
diff --git a/dd-smoke-tests/apm-tracing-disabled/src/main/java/datadog/smoketest/apmtracingdisabled/AppConfig.java b/dd-smoke-tests/apm-tracing-disabled/application/src/main/java/datadog/smoketest/apmtracingdisabled/AppConfig.java
similarity index 100%
rename from dd-smoke-tests/apm-tracing-disabled/src/main/java/datadog/smoketest/apmtracingdisabled/AppConfig.java
rename to dd-smoke-tests/apm-tracing-disabled/application/src/main/java/datadog/smoketest/apmtracingdisabled/AppConfig.java
diff --git a/dd-smoke-tests/apm-tracing-disabled/src/main/java/datadog/smoketest/apmtracingdisabled/Controller.java b/dd-smoke-tests/apm-tracing-disabled/application/src/main/java/datadog/smoketest/apmtracingdisabled/Controller.java
similarity index 100%
rename from dd-smoke-tests/apm-tracing-disabled/src/main/java/datadog/smoketest/apmtracingdisabled/Controller.java
rename to dd-smoke-tests/apm-tracing-disabled/application/src/main/java/datadog/smoketest/apmtracingdisabled/Controller.java
diff --git a/dd-smoke-tests/apm-tracing-disabled/src/main/java/datadog/smoketest/apmtracingdisabled/SpringbootApplication.java b/dd-smoke-tests/apm-tracing-disabled/application/src/main/java/datadog/smoketest/apmtracingdisabled/SpringbootApplication.java
similarity index 100%
rename from dd-smoke-tests/apm-tracing-disabled/src/main/java/datadog/smoketest/apmtracingdisabled/SpringbootApplication.java
rename to dd-smoke-tests/apm-tracing-disabled/application/src/main/java/datadog/smoketest/apmtracingdisabled/SpringbootApplication.java
diff --git a/dd-smoke-tests/apm-tracing-disabled/build.gradle b/dd-smoke-tests/apm-tracing-disabled/build.gradle
index 638260752db..4fb376331f9 100644
--- a/dd-smoke-tests/apm-tracing-disabled/build.gradle
+++ b/dd-smoke-tests/apm-tracing-disabled/build.gradle
@@ -1,36 +1,63 @@
-import org.springframework.boot.gradle.tasks.bundling.BootJar
+apply from: "$rootDir/gradle/java.gradle"
 
-plugins {
-  id 'java'
-  id 'org.springframework.boot' version '2.7.15'
-  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
-  id 'java-test-fixtures'
-}
+apply plugin: 'java-test-fixtures'
 
-apply from: "$rootDir/gradle/java.gradle"
-apply from: "$rootDir/gradle/spring-boot-plugin.gradle"
 description = 'ASM Standalone Billing Tests.'
 
-java {
-  sourceCompatibility = '1.8'
+def appDir = "$projectDir/application"
+def appBuildDir = "$buildDir/application"
+def isWindows = System.getProperty("os.name").toLowerCase().contains("win")
+def gradlewCommand = isWindows ? 'gradlew.bat' : 'gradlew'
+
+tasks.register('bootJar', Exec) {
+  workingDir appDir
+  environment += [
+    "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
+    "JAVA_HOME": getLazyJavaHomeFor(8)
+  ]
+  commandLine "$appDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir",
+    "-PapiJar=${project(':dd-trace-api').tasks.jar.archiveFile.get()}"
+
+  outputs.cacheIf { true }
+
+  outputs.dir(appBuildDir)
+    .withPropertyName("applicationJar")
+
+  inputs.files(fileTree(appDir) {
+    include '**/*'
+    exclude '.gradle/**'
+  })
+  .withPropertyName("application")
+  .withPathSensitivity(PathSensitivity.RELATIVE)
+}
+
+tasks.named('bootJar', Exec) {
+  dependsOn project(':dd-trace-api').tasks.named('jar')
 }
 
 dependencies {
-  implementation 'org.springframework.boot:spring-boot-starter-web'
-  implementation group: 'io.opentracing', name: 'opentracing-api', version: '0.32.0'
-  implementation group: 'io.opentracing', name: 'opentracing-util', version: '0.32.0'
-  implementation project(':dd-trace-api')
   testImplementation project(':dd-smoke-tests')
   testImplementation(testFixtures(project(":dd-smoke-tests:iast-util")))
 }
 
 tasks.withType(Test).configureEach {
-  def bootJarTask = tasks.named('bootJar', BootJar)
-  dependsOn bootJarTask
+  dependsOn 'bootJar'
   jvmArgumentProviders.add(new CommandLineArgumentProvider() {
       @Override
       Iterable<String> asArguments() {
-        return bootJarTask.map { ["-Ddatadog.smoketest.springboot.shadowJar.path=${it.archiveFile.get()}"] }.get()
+        return [
+          "-Ddatadog.smoketest.springboot.shadowJar.path=$appBuildDir/libs/apm-tracing-disabled-smoketest.jar"
+        ]
       }
     })
 }
+
+spotless {
+  java {
+    target "**/*.java"
+  }
+
+  groovyGradle {
+    target '*.gradle', "**/*.gradle"
+  }
+}
diff --git a/dd-smoke-tests/datastreams/kafkaschemaregistry/build.gradle b/dd-smoke-tests/datastreams/kafkaschemaregistry/build.gradle
index fe525e8a70e..502d39ba6f7 100644
--- a/dd-smoke-tests/datastreams/kafkaschemaregistry/build.gradle
+++ b/dd-smoke-tests/datastreams/kafkaschemaregistry/build.gradle
@@ -3,11 +3,9 @@ import com.github.jengelman.gradle.plugins.shadow.tasks.ShadowJar
 plugins {
   id 'com.gradleup.shadow'
   id 'java'
-  id 'org.springframework.boot' version '2.6.3'
 }
 
 apply from: "$rootDir/gradle/java.gradle"
-apply from: "$rootDir/gradle/spring-boot-plugin.gradle"
 description = 'Kafka Smoke Tests.'
 
 tasks.named("jar", Jar) {
diff --git a/dd-smoke-tests/kafka-2/application/build.gradle b/dd-smoke-tests/kafka-2/application/build.gradle
new file mode 100644
index 00000000000..f5ffc8e910c
--- /dev/null
+++ b/dd-smoke-tests/kafka-2/application/build.gradle
@@ -0,0 +1,29 @@
+plugins {
+  id 'java'
+  id 'org.springframework.boot' version '2.7.15'
+  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
+}
+
+def sharedRootDir = "$rootDir/../../../"
+def sharedConfigDirectory = "$sharedRootDir/gradle"
+rootProject.ext.sharedConfigDirectory = sharedConfigDirectory
+
+apply from: "$sharedConfigDirectory/repositories.gradle"
+
+if (hasProperty('appBuildDir')) {
+  buildDir = property('appBuildDir')
+}
+
+version = ""
+
+if (hasProperty('iastUtilJar')) {
+  dependencies {
+    implementation files(property('iastUtilJar'))
+  }
+}
+
+dependencies {
+  implementation('org.springframework.boot:spring-boot-starter-web')
+  implementation('org.springframework.boot:spring-boot-starter-actuator')
+  implementation('org.springframework.kafka:spring-kafka')
+}
diff --git a/dd-smoke-tests/kafka-2/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/kafka-2/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/kafka-2/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/kafka-2/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/kafka-2/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/kafka-2/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/kafka-2/application/gradlew b/dd-smoke-tests/kafka-2/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/kafka-2/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/kafka-2/application/gradlew.bat b/dd-smoke-tests/kafka-2/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/kafka-2/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/kafka-2/application/settings.gradle b/dd-smoke-tests/kafka-2/application/settings.gradle
new file mode 100644
index 00000000000..68e9ddb0060
--- /dev/null
+++ b/dd-smoke-tests/kafka-2/application/settings.gradle
@@ -0,0 +1,32 @@
+pluginManagement {
+  repositories {
+    mavenLocal()
+    if (settings.hasProperty("gradlePluginProxy")) {
+      maven {
+        url settings["gradlePluginProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    if (settings.hasProperty("mavenRepositoryProxy")) {
+      maven {
+        url settings["mavenRepositoryProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    gradlePluginPortal()
+    mavenCentral()
+  }
+}
+
+def isCI = providers.environmentVariable("CI").isPresent()
+
+if (isCI) {
+  def sharedRootDir = "$rootDir/../../../"
+  buildCache {
+    local {
+      directory = "$sharedRootDir/workspace/build-cache"
+    }
+  }
+}
+
+rootProject.name='kafka-2-smoketest'
diff --git a/dd-smoke-tests/kafka-2/src/main/java/datadog/smoketest/kafka/KafkaApplication.java b/dd-smoke-tests/kafka-2/application/src/main/java/datadog/smoketest/kafka/KafkaApplication.java
similarity index 100%
rename from dd-smoke-tests/kafka-2/src/main/java/datadog/smoketest/kafka/KafkaApplication.java
rename to dd-smoke-tests/kafka-2/application/src/main/java/datadog/smoketest/kafka/KafkaApplication.java
diff --git a/dd-smoke-tests/kafka-2/src/main/java/datadog/smoketest/kafka/iast/IastConfiguration.java b/dd-smoke-tests/kafka-2/application/src/main/java/datadog/smoketest/kafka/iast/IastConfiguration.java
similarity index 100%
rename from dd-smoke-tests/kafka-2/src/main/java/datadog/smoketest/kafka/iast/IastConfiguration.java
rename to dd-smoke-tests/kafka-2/application/src/main/java/datadog/smoketest/kafka/iast/IastConfiguration.java
diff --git a/dd-smoke-tests/kafka-2/src/main/java/datadog/smoketest/kafka/iast/IastController.java b/dd-smoke-tests/kafka-2/application/src/main/java/datadog/smoketest/kafka/iast/IastController.java
similarity index 100%
rename from dd-smoke-tests/kafka-2/src/main/java/datadog/smoketest/kafka/iast/IastController.java
rename to dd-smoke-tests/kafka-2/application/src/main/java/datadog/smoketest/kafka/iast/IastController.java
diff --git a/dd-smoke-tests/kafka-2/src/main/java/datadog/smoketest/kafka/iast/IastMessage.java b/dd-smoke-tests/kafka-2/application/src/main/java/datadog/smoketest/kafka/iast/IastMessage.java
similarity index 100%
rename from dd-smoke-tests/kafka-2/src/main/java/datadog/smoketest/kafka/iast/IastMessage.java
rename to dd-smoke-tests/kafka-2/application/src/main/java/datadog/smoketest/kafka/iast/IastMessage.java
diff --git a/dd-smoke-tests/kafka-2/build.gradle b/dd-smoke-tests/kafka-2/build.gradle
index c947425a4ba..39cf19714ce 100644
--- a/dd-smoke-tests/kafka-2/build.gradle
+++ b/dd-smoke-tests/kafka-2/build.gradle
@@ -1,34 +1,62 @@
-import org.springframework.boot.gradle.tasks.bundling.BootJar
+apply from: "$rootDir/gradle/java.gradle"
 
-plugins {
-  id 'org.springframework.boot' version '2.7.15'
-  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
-  id 'java-test-fixtures'
-}
+apply plugin: 'java-test-fixtures'
 
-apply from: "$rootDir/gradle/java.gradle"
-apply from: "$rootDir/gradle/spring-boot-plugin.gradle"
 description = 'Kafka 2.x Smoke Tests.'
 
-dependencies {
-  implementation('org.springframework.boot:spring-boot-starter-web')
-  implementation('org.springframework.boot:spring-boot-starter-actuator')
-  implementation('org.springframework.kafka:spring-kafka')
+def appDir = "$projectDir/application"
+def appBuildDir = "$buildDir/application"
+def isWindows = System.getProperty("os.name").toLowerCase().contains("win")
+def gradlewCommand = isWindows ? 'gradlew.bat' : 'gradlew'
+
+tasks.register('bootJar', Exec) {
+  workingDir appDir
+  environment += [
+    "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
+    "JAVA_HOME": getLazyJavaHomeFor(8)
+  ]
+  commandLine "$appDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir",
+    "-PiastUtilJar=${project(':dd-smoke-tests:iast-util').tasks.jar.archiveFile.get()}"
+
+  outputs.cacheIf { true }
+
+  outputs.dir(appBuildDir)
+    .withPropertyName("applicationJar")
 
-  testImplementation('org.springframework.kafka:spring-kafka-test')
+  inputs.files(fileTree(appDir) {
+    include '**/*'
+    exclude '.gradle/**'
+  })
+  .withPropertyName("application")
+  .withPathSensitivity(PathSensitivity.RELATIVE)
+}
+
+tasks.named('bootJar', Exec) {
+  dependsOn project(':dd-smoke-tests:iast-util').tasks.named('jar')
+}
 
+dependencies {
+  testImplementation('org.springframework.kafka:spring-kafka-test:2.8.11')
   testImplementation project(':dd-smoke-tests')
-  implementation project(':dd-smoke-tests:iast-util')
   testImplementation(testFixtures(project(":dd-smoke-tests:iast-util")))
 }
 
 tasks.withType(Test).configureEach {
-  def bootJarTask = tasks.named('bootJar', BootJar)
-  dependsOn bootJarTask
+  dependsOn 'bootJar'
   jvmArgumentProviders.add(new CommandLineArgumentProvider() {
       @Override
       Iterable<String> asArguments() {
-        return bootJarTask.map { ["-Ddatadog.smoketest.springboot.shadowJar.path=${it.archiveFile.get()}"] }.get()
+        return ["-Ddatadog.smoketest.springboot.shadowJar.path=$appBuildDir/libs/kafka-2-smoketest.jar"]
       }
     })
 }
+
+spotless {
+  java {
+    target "**/*.java"
+  }
+
+  groovyGradle {
+    target '*.gradle', "**/*.gradle"
+  }
+}
diff --git a/dd-smoke-tests/kafka-3/application/.gitignore b/dd-smoke-tests/kafka-3/application/.gitignore
index 1ec2c548b11..c676bce300c 100644
--- a/dd-smoke-tests/kafka-3/application/.gitignore
+++ b/dd-smoke-tests/kafka-3/application/.gitignore
@@ -1,6 +1,3 @@
-# Ignore all project specific gradle directories/files
+# Ignore build artifacts
 .gradle
-gradle
 build
-gradlew
-gradlew.bat
diff --git a/dd-smoke-tests/kafka-3/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/kafka-3/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/kafka-3/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/kafka-3/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/kafka-3/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/kafka-3/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/kafka-3/application/gradlew b/dd-smoke-tests/kafka-3/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/kafka-3/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/kafka-3/application/gradlew.bat b/dd-smoke-tests/kafka-3/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/kafka-3/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/kafka-3/build.gradle b/dd-smoke-tests/kafka-3/build.gradle
index 0c92600de50..e0e929a2287 100644
--- a/dd-smoke-tests/kafka-3/build.gradle
+++ b/dd-smoke-tests/kafka-3/build.gradle
@@ -26,7 +26,7 @@ tasks.register('bootJar', Exec) {
     "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
     "JAVA_HOME": getLazyJavaHomeFor(17)
   ]
-  commandLine "$rootDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir"
+  commandLine "$appDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir"
 
   outputs.cacheIf { true }
 
diff --git a/dd-smoke-tests/openfeature/application/build.gradle b/dd-smoke-tests/openfeature/application/build.gradle
new file mode 100644
index 00000000000..a74020164f9
--- /dev/null
+++ b/dd-smoke-tests/openfeature/application/build.gradle
@@ -0,0 +1,35 @@
+plugins {
+  id 'java'
+  id 'org.springframework.boot' version '2.7.15'
+  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
+}
+
+def sharedRootDir = "$rootDir/../../../"
+def sharedConfigDirectory = "$sharedRootDir/gradle"
+rootProject.ext.sharedConfigDirectory = sharedConfigDirectory
+
+apply from: "$sharedConfigDirectory/repositories.gradle"
+
+if (hasProperty('appBuildDir')) {
+  buildDir = property('appBuildDir')
+}
+
+version = ""
+
+java {
+  sourceCompatibility = 11
+  targetCompatibility = 11
+}
+
+if (hasProperty('featureFlaggingApiJar')) {
+  dependencies {
+    implementation files(property('featureFlaggingApiJar'))
+  }
+}
+
+dependencies {
+  // OpenFeature SDK is an API dependency of feature-flagging-api but is not
+  // transitively resolved when the jar is passed as a files() dependency.
+  implementation 'dev.openfeature:sdk:1.20.1'
+  implementation 'org.springframework.boot:spring-boot-starter-web'
+}
diff --git a/dd-smoke-tests/openfeature/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/openfeature/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/openfeature/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/openfeature/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/openfeature/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/openfeature/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/openfeature/application/gradlew b/dd-smoke-tests/openfeature/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/openfeature/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/openfeature/application/gradlew.bat b/dd-smoke-tests/openfeature/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/openfeature/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/openfeature/application/settings.gradle b/dd-smoke-tests/openfeature/application/settings.gradle
new file mode 100644
index 00000000000..b326d9873f1
--- /dev/null
+++ b/dd-smoke-tests/openfeature/application/settings.gradle
@@ -0,0 +1,32 @@
+pluginManagement {
+  repositories {
+    mavenLocal()
+    if (settings.hasProperty("gradlePluginProxy")) {
+      maven {
+        url settings["gradlePluginProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    if (settings.hasProperty("mavenRepositoryProxy")) {
+      maven {
+        url settings["mavenRepositoryProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    gradlePluginPortal()
+    mavenCentral()
+  }
+}
+
+def isCI = providers.environmentVariable("CI").isPresent()
+
+if (isCI) {
+  def sharedRootDir = "$rootDir/../../../"
+  buildCache {
+    local {
+      directory = "$sharedRootDir/workspace/build-cache"
+    }
+  }
+}
+
+rootProject.name='openfeature-smoketest'
diff --git a/dd-smoke-tests/openfeature/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java b/dd-smoke-tests/openfeature/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
similarity index 100%
rename from dd-smoke-tests/openfeature/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
rename to dd-smoke-tests/openfeature/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
diff --git a/dd-smoke-tests/openfeature/src/main/java/datadog/smoketest/springboot/openfeature/OpenFeatureConfiguration.java b/dd-smoke-tests/openfeature/application/src/main/java/datadog/smoketest/springboot/openfeature/OpenFeatureConfiguration.java
similarity index 100%
rename from dd-smoke-tests/openfeature/src/main/java/datadog/smoketest/springboot/openfeature/OpenFeatureConfiguration.java
rename to dd-smoke-tests/openfeature/application/src/main/java/datadog/smoketest/springboot/openfeature/OpenFeatureConfiguration.java
diff --git a/dd-smoke-tests/openfeature/src/main/java/datadog/smoketest/springboot/openfeature/OpenFeatureController.java b/dd-smoke-tests/openfeature/application/src/main/java/datadog/smoketest/springboot/openfeature/OpenFeatureController.java
similarity index 100%
rename from dd-smoke-tests/openfeature/src/main/java/datadog/smoketest/springboot/openfeature/OpenFeatureController.java
rename to dd-smoke-tests/openfeature/application/src/main/java/datadog/smoketest/springboot/openfeature/OpenFeatureController.java
diff --git a/dd-smoke-tests/openfeature/build.gradle b/dd-smoke-tests/openfeature/build.gradle
index a38696418ef..d943be32ae4 100644
--- a/dd-smoke-tests/openfeature/build.gradle
+++ b/dd-smoke-tests/openfeature/build.gradle
@@ -1,38 +1,63 @@
-import org.springframework.boot.gradle.tasks.bundling.BootJar
-
-plugins {
-  id 'java'
-  id 'org.springframework.boot' version '2.7.15'
-  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
-}
-
 apply from: "$rootDir/gradle/java.gradle"
-apply from: "$rootDir/gradle/spring-boot-plugin.gradle"
+
 description = 'Open Feature provider Smoke Tests.'
 
 testJvmConstraints {
   minJavaVersion = JavaVersion.VERSION_11
 }
 
-tasks.named("compileJava", JavaCompile) {
-  configureCompiler(it, 11, JavaVersion.VERSION_11)
+def appDir = "$projectDir/application"
+def appBuildDir = "$buildDir/application"
+def isWindows = System.getProperty("os.name").toLowerCase().contains("win")
+def gradlewCommand = isWindows ? 'gradlew.bat' : 'gradlew'
+
+tasks.register('bootJar', Exec) {
+  workingDir appDir
+  environment += [
+    "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
+    "JAVA_HOME": getLazyJavaHomeFor(11)
+  ]
+  commandLine "$appDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir",
+    "-PfeatureFlaggingApiJar=${project(':products:feature-flagging:feature-flagging-api').tasks.jar.archiveFile.get()}"
+
+  outputs.cacheIf { true }
+
+  outputs.dir(appBuildDir)
+    .withPropertyName("applicationJar")
+
+  inputs.files(fileTree(appDir) {
+    include '**/*'
+    exclude '.gradle/**'
+  })
+  .withPropertyName("application")
+  .withPathSensitivity(PathSensitivity.RELATIVE)
+}
+
+tasks.named('bootJar', Exec) {
+  dependsOn project(':products:feature-flagging:feature-flagging-api').tasks.named('jar')
 }
 
 dependencies {
-  implementation project(':products:feature-flagging:feature-flagging-api')
-  implementation 'org.springframework.boot:spring-boot-starter-web'
-
   testImplementation project(':dd-smoke-tests')
   testImplementation project(':products:feature-flagging:feature-flagging-lib')
 }
 
 tasks.withType(Test).configureEach {
-  dependsOn "bootJar"
-  def bootJarTask = tasks.named('bootJar', BootJar)
+  dependsOn 'bootJar'
   jvmArgumentProviders.add(new CommandLineArgumentProvider() {
       @Override
       Iterable<String> asArguments() {
-        return bootJarTask.map { ["-Ddatadog.smoketest.springboot.shadowJar.path=${it.archiveFile.get()}"] }.get()
+        return ["-Ddatadog.smoketest.springboot.shadowJar.path=$appBuildDir/libs/openfeature-smoketest.jar"]
       }
     })
 }
+
+spotless {
+  java {
+    target "**/*.java"
+  }
+
+  groovyGradle {
+    target '*.gradle', "**/*.gradle"
+  }
+}
diff --git a/dd-smoke-tests/spring-boot-2.7-webflux/application/.gitignore b/dd-smoke-tests/spring-boot-2.7-webflux/application/.gitignore
index 1ec2c548b11..c676bce300c 100644
--- a/dd-smoke-tests/spring-boot-2.7-webflux/application/.gitignore
+++ b/dd-smoke-tests/spring-boot-2.7-webflux/application/.gitignore
@@ -1,6 +1,3 @@
-# Ignore all project specific gradle directories/files
+# Ignore build artifacts
 .gradle
-gradle
 build
-gradlew
-gradlew.bat
diff --git a/dd-smoke-tests/spring-boot-2.7-webflux/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/spring-boot-2.7-webflux/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/spring-boot-2.7-webflux/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/spring-boot-2.7-webflux/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/spring-boot-2.7-webflux/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/spring-boot-2.7-webflux/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/spring-boot-2.7-webflux/application/gradlew b/dd-smoke-tests/spring-boot-2.7-webflux/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/spring-boot-2.7-webflux/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/spring-boot-2.7-webflux/application/gradlew.bat b/dd-smoke-tests/spring-boot-2.7-webflux/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/spring-boot-2.7-webflux/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/spring-boot-2.7-webflux/build.gradle b/dd-smoke-tests/spring-boot-2.7-webflux/build.gradle
index ec403dc3c20..a76e3066d06 100644
--- a/dd-smoke-tests/spring-boot-2.7-webflux/build.gradle
+++ b/dd-smoke-tests/spring-boot-2.7-webflux/build.gradle
@@ -18,7 +18,7 @@ tasks.register('webfluxBuild', Exec) {
     "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
     "JAVA_HOME": getLazyJavaHomeFor(8)
   ]
-  commandLine "$rootDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir", "-PapiJar=${project(':dd-trace-api').tasks.jar.archiveFile.get()}"
+  commandLine "$appDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir", "-PapiJar=${project(':dd-trace-api').tasks.jar.archiveFile.get()}"
 
   outputs.cacheIf { true }
 
diff --git a/dd-smoke-tests/spring-boot-3.0-native/application/.gitignore b/dd-smoke-tests/spring-boot-3.0-native/application/.gitignore
index 1ec2c548b11..c676bce300c 100644
--- a/dd-smoke-tests/spring-boot-3.0-native/application/.gitignore
+++ b/dd-smoke-tests/spring-boot-3.0-native/application/.gitignore
@@ -1,6 +1,3 @@
-# Ignore all project specific gradle directories/files
+# Ignore build artifacts
 .gradle
-gradle
 build
-gradlew
-gradlew.bat
diff --git a/dd-smoke-tests/spring-boot-3.0-native/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/spring-boot-3.0-native/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/spring-boot-3.0-native/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/spring-boot-3.0-native/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/spring-boot-3.0-native/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/spring-boot-3.0-native/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/spring-boot-3.0-native/application/gradlew b/dd-smoke-tests/spring-boot-3.0-native/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/spring-boot-3.0-native/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/spring-boot-3.0-native/application/gradlew.bat b/dd-smoke-tests/spring-boot-3.0-native/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/spring-boot-3.0-native/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/spring-boot-3.0-native/build.gradle b/dd-smoke-tests/spring-boot-3.0-native/build.gradle
index e0dda4c6db6..c61d62d010a 100644
--- a/dd-smoke-tests/spring-boot-3.0-native/build.gradle
+++ b/dd-smoke-tests/spring-boot-3.0-native/build.gradle
@@ -37,7 +37,7 @@ if (testGraalvmVersion >= 17) {
       'NATIVE_IMAGE_DEPRECATED_BUILDER_SANITATION' : 'true'
     ]
     commandLine(
-      "$rootDir/${gradlewCommand}",
+      "$appDir/${gradlewCommand}",
       'nativeCompile',
       '--no-daemon',
       '--max-workers=4',
diff --git a/dd-smoke-tests/spring-boot-3.0-webflux/application/.gitignore b/dd-smoke-tests/spring-boot-3.0-webflux/application/.gitignore
index 1ec2c548b11..c676bce300c 100644
--- a/dd-smoke-tests/spring-boot-3.0-webflux/application/.gitignore
+++ b/dd-smoke-tests/spring-boot-3.0-webflux/application/.gitignore
@@ -1,6 +1,3 @@
-# Ignore all project specific gradle directories/files
+# Ignore build artifacts
 .gradle
-gradle
 build
-gradlew
-gradlew.bat
diff --git a/dd-smoke-tests/spring-boot-3.0-webflux/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/spring-boot-3.0-webflux/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/spring-boot-3.0-webflux/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/spring-boot-3.0-webflux/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/spring-boot-3.0-webflux/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/spring-boot-3.0-webflux/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/spring-boot-3.0-webflux/application/gradlew b/dd-smoke-tests/spring-boot-3.0-webflux/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/spring-boot-3.0-webflux/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/spring-boot-3.0-webflux/application/gradlew.bat b/dd-smoke-tests/spring-boot-3.0-webflux/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/spring-boot-3.0-webflux/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/spring-boot-3.0-webflux/build.gradle b/dd-smoke-tests/spring-boot-3.0-webflux/build.gradle
index 6138aef945d..28b12fbc45d 100644
--- a/dd-smoke-tests/spring-boot-3.0-webflux/build.gradle
+++ b/dd-smoke-tests/spring-boot-3.0-webflux/build.gradle
@@ -22,7 +22,7 @@ tasks.register('webfluxBuild30', Exec) {
     "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
     "JAVA_HOME": getLazyJavaHomeFor(17)
   ]
-  commandLine "$rootDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir", "-PapiJar=${project(':dd-trace-api').tasks.jar.archiveFile.get()}"
+  commandLine "$appDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir", "-PapiJar=${project(':dd-trace-api').tasks.jar.archiveFile.get()}"
 
   outputs.cacheIf { true }
 
diff --git a/dd-smoke-tests/spring-boot-3.0-webmvc/application/.gitignore b/dd-smoke-tests/spring-boot-3.0-webmvc/application/.gitignore
index 1ec2c548b11..c676bce300c 100644
--- a/dd-smoke-tests/spring-boot-3.0-webmvc/application/.gitignore
+++ b/dd-smoke-tests/spring-boot-3.0-webmvc/application/.gitignore
@@ -1,6 +1,3 @@
-# Ignore all project specific gradle directories/files
+# Ignore build artifacts
 .gradle
-gradle
 build
-gradlew
-gradlew.bat
diff --git a/dd-smoke-tests/spring-boot-3.0-webmvc/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/spring-boot-3.0-webmvc/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/spring-boot-3.0-webmvc/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/spring-boot-3.0-webmvc/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/spring-boot-3.0-webmvc/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/spring-boot-3.0-webmvc/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/spring-boot-3.0-webmvc/application/gradlew b/dd-smoke-tests/spring-boot-3.0-webmvc/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/spring-boot-3.0-webmvc/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/spring-boot-3.0-webmvc/application/gradlew.bat b/dd-smoke-tests/spring-boot-3.0-webmvc/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/spring-boot-3.0-webmvc/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/spring-boot-3.0-webmvc/build.gradle b/dd-smoke-tests/spring-boot-3.0-webmvc/build.gradle
index 46c00fbcec8..d6fbc30b1f6 100644
--- a/dd-smoke-tests/spring-boot-3.0-webmvc/build.gradle
+++ b/dd-smoke-tests/spring-boot-3.0-webmvc/build.gradle
@@ -22,7 +22,7 @@ tasks.register('webmvcBuild30', Exec) {
     "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
     "JAVA_HOME": getLazyJavaHomeFor(17)
   ]
-  commandLine "$rootDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir", "-PapiJar=${project(':dd-trace-api').tasks.jar.archiveFile.get()}"
+  commandLine "$appDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir", "-PapiJar=${project(':dd-trace-api').tasks.jar.archiveFile.get()}"
 
   outputs.cacheIf { true }
 
diff --git a/dd-smoke-tests/spring-boot-3.3-webmvc/application/.gitignore b/dd-smoke-tests/spring-boot-3.3-webmvc/application/.gitignore
index 1ec2c548b11..c676bce300c 100644
--- a/dd-smoke-tests/spring-boot-3.3-webmvc/application/.gitignore
+++ b/dd-smoke-tests/spring-boot-3.3-webmvc/application/.gitignore
@@ -1,6 +1,3 @@
-# Ignore all project specific gradle directories/files
+# Ignore build artifacts
 .gradle
-gradle
 build
-gradlew
-gradlew.bat
diff --git a/dd-smoke-tests/spring-boot-3.3-webmvc/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/spring-boot-3.3-webmvc/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/spring-boot-3.3-webmvc/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/spring-boot-3.3-webmvc/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/spring-boot-3.3-webmvc/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/spring-boot-3.3-webmvc/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/spring-boot-3.3-webmvc/application/gradlew b/dd-smoke-tests/spring-boot-3.3-webmvc/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/spring-boot-3.3-webmvc/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/spring-boot-3.3-webmvc/application/gradlew.bat b/dd-smoke-tests/spring-boot-3.3-webmvc/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/spring-boot-3.3-webmvc/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/spring-boot-3.3-webmvc/build.gradle b/dd-smoke-tests/spring-boot-3.3-webmvc/build.gradle
index 484ecfc5668..9bf982fab30 100644
--- a/dd-smoke-tests/spring-boot-3.3-webmvc/build.gradle
+++ b/dd-smoke-tests/spring-boot-3.3-webmvc/build.gradle
@@ -22,7 +22,7 @@ tasks.register('webmvcBuild3', Exec) {
     "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
     "JAVA_HOME": getLazyJavaHomeFor(17)
   ]
-  commandLine "$rootDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir", "-PapiJar=${project(':dd-trace-api').tasks.jar.archiveFile.get()}"
+  commandLine "$appDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir", "-PapiJar=${project(':dd-trace-api').tasks.jar.archiveFile.get()}"
 
   outputs.cacheIf { true }
 
diff --git a/dd-smoke-tests/springboot-freemarker/application/build.gradle b/dd-smoke-tests/springboot-freemarker/application/build.gradle
new file mode 100644
index 00000000000..3a0220c4ca8
--- /dev/null
+++ b/dd-smoke-tests/springboot-freemarker/application/build.gradle
@@ -0,0 +1,26 @@
+plugins {
+  id 'java'
+  id 'org.springframework.boot' version '2.7.15'
+  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
+}
+
+def sharedRootDir = "$rootDir/../../../"
+def sharedConfigDirectory = "$sharedRootDir/gradle"
+rootProject.ext.sharedConfigDirectory = sharedConfigDirectory
+
+apply from: "$sharedConfigDirectory/repositories.gradle"
+
+if (hasProperty('appBuildDir')) {
+  buildDir = property('appBuildDir')
+}
+
+version = ""
+
+java {
+  sourceCompatibility = '1.8'
+}
+
+dependencies {
+  implementation group: 'org.springframework.boot', name: 'spring-boot-starter-web', version: '1.5.18.RELEASE'
+  implementation group: 'org.freemarker', name: 'freemarker', version: '2.3.24-incubating'
+}
diff --git a/dd-smoke-tests/springboot-freemarker/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/springboot-freemarker/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/springboot-freemarker/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/springboot-freemarker/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/springboot-freemarker/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/springboot-freemarker/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/springboot-freemarker/application/gradlew b/dd-smoke-tests/springboot-freemarker/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/springboot-freemarker/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/springboot-freemarker/application/gradlew.bat b/dd-smoke-tests/springboot-freemarker/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/springboot-freemarker/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/springboot-freemarker/application/settings.gradle b/dd-smoke-tests/springboot-freemarker/application/settings.gradle
new file mode 100644
index 00000000000..f202c747c3e
--- /dev/null
+++ b/dd-smoke-tests/springboot-freemarker/application/settings.gradle
@@ -0,0 +1,32 @@
+pluginManagement {
+  repositories {
+    mavenLocal()
+    if (settings.hasProperty("gradlePluginProxy")) {
+      maven {
+        url settings["gradlePluginProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    if (settings.hasProperty("mavenRepositoryProxy")) {
+      maven {
+        url settings["mavenRepositoryProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    gradlePluginPortal()
+    mavenCentral()
+  }
+}
+
+def isCI = providers.environmentVariable("CI").isPresent()
+
+if (isCI) {
+  def sharedRootDir = "$rootDir/../../../"
+  buildCache {
+    local {
+      directory = "$sharedRootDir/workspace/build-cache"
+    }
+  }
+}
+
+rootProject.name='springboot-freemarker-smoketest'
diff --git a/dd-smoke-tests/springboot-freemarker/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java b/dd-smoke-tests/springboot-freemarker/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
similarity index 100%
rename from dd-smoke-tests/springboot-freemarker/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
rename to dd-smoke-tests/springboot-freemarker/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
diff --git a/dd-smoke-tests/springboot-freemarker/src/main/java/datadog/smoketest/springboot/XssController.java b/dd-smoke-tests/springboot-freemarker/application/src/main/java/datadog/smoketest/springboot/XssController.java
similarity index 100%
rename from dd-smoke-tests/springboot-freemarker/src/main/java/datadog/smoketest/springboot/XssController.java
rename to dd-smoke-tests/springboot-freemarker/application/src/main/java/datadog/smoketest/springboot/XssController.java
diff --git a/dd-smoke-tests/springboot-freemarker/src/main/resources/templates/freemarker-2.3.24-insecure.ftlh b/dd-smoke-tests/springboot-freemarker/application/src/main/resources/templates/freemarker-2.3.24-insecure.ftlh
similarity index 100%
rename from dd-smoke-tests/springboot-freemarker/src/main/resources/templates/freemarker-2.3.24-insecure.ftlh
rename to dd-smoke-tests/springboot-freemarker/application/src/main/resources/templates/freemarker-2.3.24-insecure.ftlh
diff --git a/dd-smoke-tests/springboot-freemarker/src/main/resources/templates/freemarker-2.3.24-secure.ftlh b/dd-smoke-tests/springboot-freemarker/application/src/main/resources/templates/freemarker-2.3.24-secure.ftlh
similarity index 100%
rename from dd-smoke-tests/springboot-freemarker/src/main/resources/templates/freemarker-2.3.24-secure.ftlh
rename to dd-smoke-tests/springboot-freemarker/application/src/main/resources/templates/freemarker-2.3.24-secure.ftlh
diff --git a/dd-smoke-tests/springboot-freemarker/src/main/resources/templates/freemarker-2.3.9-insecure.ftlh b/dd-smoke-tests/springboot-freemarker/application/src/main/resources/templates/freemarker-2.3.9-insecure.ftlh
similarity index 100%
rename from dd-smoke-tests/springboot-freemarker/src/main/resources/templates/freemarker-2.3.9-insecure.ftlh
rename to dd-smoke-tests/springboot-freemarker/application/src/main/resources/templates/freemarker-2.3.9-insecure.ftlh
diff --git a/dd-smoke-tests/springboot-freemarker/src/main/resources/templates/freemarker-2.3.9-secure.ftlh b/dd-smoke-tests/springboot-freemarker/application/src/main/resources/templates/freemarker-2.3.9-secure.ftlh
similarity index 100%
rename from dd-smoke-tests/springboot-freemarker/src/main/resources/templates/freemarker-2.3.9-secure.ftlh
rename to dd-smoke-tests/springboot-freemarker/application/src/main/resources/templates/freemarker-2.3.9-secure.ftlh
diff --git a/dd-smoke-tests/springboot-freemarker/build.gradle b/dd-smoke-tests/springboot-freemarker/build.gradle
index 57c7a4e9eb1..ab6cf36bbcf 100644
--- a/dd-smoke-tests/springboot-freemarker/build.gradle
+++ b/dd-smoke-tests/springboot-freemarker/build.gradle
@@ -1,35 +1,72 @@
-import org.springframework.boot.gradle.tasks.bundling.BootJar
+apply from: "$rootDir/gradle/java.gradle"
 
-plugins {
-  id 'java'
-  id 'org.springframework.boot' version '2.7.15'
-  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
-  id 'java-test-fixtures'
-}
+apply plugin: 'java-test-fixtures'
 
-apply from: "$rootDir/gradle/java.gradle"
-apply from: "$rootDir/gradle/spring-boot-plugin.gradle"
 description = 'SpringBoot Freemarker Smoke Tests.'
 
-java {
-  sourceCompatibility = '1.8'
+def appDir = "$projectDir/application"
+def appBuildDir = "$buildDir/application"
+def isWindows = System.getProperty("os.name").toLowerCase().contains("win")
+def gradlewCommand = isWindows ? 'gradlew.bat' : 'gradlew'
+
+tasks.register('bootJar', Exec) {
+  workingDir appDir
+  environment += [
+    "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
+    "JAVA_HOME": getLazyJavaHomeFor(8)
+  ]
+  commandLine "$appDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir"
+
+  outputs.cacheIf { true }
+
+  outputs.dir(appBuildDir)
+    .withPropertyName("applicationJar")
+
+  inputs.files(fileTree(appDir) {
+    include '**/*'
+    exclude '.gradle/**'
+  })
+  .withPropertyName("application")
+  .withPathSensitivity(PathSensitivity.RELATIVE)
 }
 
 dependencies {
-  implementation group: 'org.springframework.boot', name: 'spring-boot-starter-web', version: '1.5.18.RELEASE'
-  implementation group: 'org.freemarker', name: 'freemarker', version: '2.3.24-incubating'
-
   testImplementation project(':dd-smoke-tests')
   testImplementation(testFixtures(project(":dd-smoke-tests:iast-util")))
 }
 
+// The XssController loads templates from the filesystem at "resources/main/templates"
+// relative to the test's working directory (= this module's buildDir). Mirror the app's
+// processed resources here so the path resolves correctly at runtime.
+tasks.register('copyAppResources', Copy) {
+  dependsOn 'bootJar'
+  from "$appBuildDir/resources/main"
+  into "$buildDir/resources/main"
+}
+
+// jar reads build/resources/main; declare the dependency so Gradle knows the ordering.
+tasks.named('jar') {
+  dependsOn 'copyAppResources'
+}
+
 tasks.withType(Test).configureEach {
-  dependsOn "bootJar"
-  def bootJarTask = tasks.named('bootJar', BootJar)
+  dependsOn 'copyAppResources'
   jvmArgumentProviders.add(new CommandLineArgumentProvider() {
       @Override
       Iterable<String> asArguments() {
-        return bootJarTask.map { ["-Ddatadog.smoketest.springboot.shadowJar.path=${it.archiveFile.get()}"] }.get()
+        return [
+          "-Ddatadog.smoketest.springboot.shadowJar.path=$appBuildDir/libs/springboot-freemarker-smoketest.jar"
+        ]
       }
     })
 }
+
+spotless {
+  java {
+    target "**/*.java"
+  }
+
+  groovyGradle {
+    target '*.gradle', "**/*.gradle"
+  }
+}
diff --git a/dd-smoke-tests/springboot-java-11/application/build.gradle b/dd-smoke-tests/springboot-java-11/application/build.gradle
new file mode 100644
index 00000000000..ea12bb0cdc4
--- /dev/null
+++ b/dd-smoke-tests/springboot-java-11/application/build.gradle
@@ -0,0 +1,31 @@
+plugins {
+  id 'java'
+  id 'org.springframework.boot' version '2.7.15'
+  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
+}
+
+def sharedRootDir = "$rootDir/../../../"
+def sharedConfigDirectory = "$sharedRootDir/gradle"
+rootProject.ext.sharedConfigDirectory = sharedConfigDirectory
+
+apply from: "$sharedConfigDirectory/repositories.gradle"
+
+if (hasProperty('appBuildDir')) {
+  buildDir = property('appBuildDir')
+}
+
+version = ""
+
+java {
+  sourceCompatibility = 11
+}
+
+if (hasProperty('iastUtil11Jar')) {
+  dependencies {
+    implementation files(property('iastUtil11Jar'))
+  }
+}
+
+dependencies {
+  implementation group: 'org.springframework.boot', name: 'spring-boot-starter-web', version: '2.2.0.RELEASE'
+}
diff --git a/dd-smoke-tests/springboot-java-11/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/springboot-java-11/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/springboot-java-11/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/springboot-java-11/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/springboot-java-11/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/springboot-java-11/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/springboot-java-11/application/gradlew b/dd-smoke-tests/springboot-java-11/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/springboot-java-11/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/springboot-java-11/application/gradlew.bat b/dd-smoke-tests/springboot-java-11/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/springboot-java-11/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/springboot-java-11/application/settings.gradle b/dd-smoke-tests/springboot-java-11/application/settings.gradle
new file mode 100644
index 00000000000..9799114b822
--- /dev/null
+++ b/dd-smoke-tests/springboot-java-11/application/settings.gradle
@@ -0,0 +1,32 @@
+pluginManagement {
+  repositories {
+    mavenLocal()
+    if (settings.hasProperty("gradlePluginProxy")) {
+      maven {
+        url settings["gradlePluginProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    if (settings.hasProperty("mavenRepositoryProxy")) {
+      maven {
+        url settings["mavenRepositoryProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    gradlePluginPortal()
+    mavenCentral()
+  }
+}
+
+def isCI = providers.environmentVariable("CI").isPresent()
+
+if (isCI) {
+  def sharedRootDir = "$rootDir/../../../"
+  buildCache {
+    local {
+      directory = "$sharedRootDir/workspace/build-cache"
+    }
+  }
+}
+
+rootProject.name='springboot-java-11-smoketest'
diff --git a/dd-smoke-tests/springboot-java-11/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java b/dd-smoke-tests/springboot-java-11/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
similarity index 100%
rename from dd-smoke-tests/springboot-java-11/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
rename to dd-smoke-tests/springboot-java-11/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
diff --git a/dd-smoke-tests/springboot-java-11/build.gradle b/dd-smoke-tests/springboot-java-11/build.gradle
index 029df98dbd8..3112f00c049 100644
--- a/dd-smoke-tests/springboot-java-11/build.gradle
+++ b/dd-smoke-tests/springboot-java-11/build.gradle
@@ -1,42 +1,66 @@
-import org.springframework.boot.gradle.tasks.bundling.BootJar
-
-plugins {
-  id 'java'
-  id 'org.springframework.boot' version '2.7.15'
-  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
-  id 'java-test-fixtures'
-}
-
 apply from: "$rootDir/gradle/java.gradle"
 
+apply plugin: 'java-test-fixtures'
+
 testJvmConstraints {
   minJavaVersion = JavaVersion.VERSION_11
 }
 
-apply from: "$rootDir/gradle/spring-boot-plugin.gradle"
 description = 'SpringBoot Java 11 Smoke Tests.'
 
-dependencies {
-  implementation group: 'org.springframework.boot', name: 'spring-boot-starter-web', version: '2.2.0.RELEASE'
+def appDir = "$projectDir/application"
+def appBuildDir = "$buildDir/application"
+def isWindows = System.getProperty("os.name").toLowerCase().contains("win")
+def gradlewCommand = isWindows ? 'gradlew.bat' : 'gradlew'
 
-  testImplementation project(':dd-smoke-tests')
-  testImplementation testFixtures(project(":dd-smoke-tests:iast-util:iast-util-11"))
-  testImplementation testFixtures(project(':dd-smoke-tests:iast-util'))
+tasks.register('bootJar', Exec) {
+  workingDir appDir
+  environment += [
+    "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
+    "JAVA_HOME": getLazyJavaHomeFor(11)
+  ]
+  commandLine "$appDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir",
+    "-PiastUtil11Jar=${project(':dd-smoke-tests:iast-util:iast-util-11').tasks.jar.archiveFile.get()}"
+
+  outputs.cacheIf { true }
+
+  outputs.dir(appBuildDir)
+    .withPropertyName("applicationJar")
 
-  implementation project(':dd-smoke-tests:iast-util:iast-util-11')
+  inputs.files(fileTree(appDir) {
+    include '**/*'
+    exclude '.gradle/**'
+  })
+  .withPropertyName("application")
+  .withPathSensitivity(PathSensitivity.RELATIVE)
 }
 
-tasks.named("compileJava", JavaCompile) {
-  configureCompiler(it, 11, JavaVersion.VERSION_11)
+tasks.named('bootJar', Exec) {
+  dependsOn project(':dd-smoke-tests:iast-util:iast-util-11').tasks.named('jar')
+}
+
+dependencies {
+  testImplementation project(':dd-smoke-tests')
+  testImplementation testFixtures(project(":dd-smoke-tests:iast-util:iast-util-11"))
+  testImplementation testFixtures(project(':dd-smoke-tests:iast-util'))
 }
 
 tasks.withType(Test).configureEach {
-  dependsOn "bootJar"
-  def bootJarTask = tasks.named('bootJar', BootJar)
+  dependsOn 'bootJar'
   jvmArgumentProviders.add(new CommandLineArgumentProvider() {
       @Override
       Iterable<String> asArguments() {
-        return bootJarTask.map { ["-Ddatadog.smoketest.springboot.shadowJar.path=${it.archiveFile.get()}"] }.get()
+        return ["-Ddatadog.smoketest.springboot.shadowJar.path=$appBuildDir/libs/springboot-java-11-smoketest.jar"]
       }
     })
 }
+
+spotless {
+  java {
+    target "**/*.java"
+  }
+
+  groovyGradle {
+    target '*.gradle', "**/*.gradle"
+  }
+}
diff --git a/dd-smoke-tests/springboot-java-17/application/build.gradle b/dd-smoke-tests/springboot-java-17/application/build.gradle
new file mode 100644
index 00000000000..413f24ce06d
--- /dev/null
+++ b/dd-smoke-tests/springboot-java-17/application/build.gradle
@@ -0,0 +1,31 @@
+plugins {
+  id 'java'
+  id 'org.springframework.boot' version '2.7.15'
+  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
+}
+
+def sharedRootDir = "$rootDir/../../../"
+def sharedConfigDirectory = "$sharedRootDir/gradle"
+rootProject.ext.sharedConfigDirectory = sharedConfigDirectory
+
+apply from: "$sharedConfigDirectory/repositories.gradle"
+
+if (hasProperty('appBuildDir')) {
+  buildDir = property('appBuildDir')
+}
+
+version = ""
+
+java {
+  sourceCompatibility = 17
+}
+
+if (hasProperty('iastUtil17Jar')) {
+  dependencies {
+    implementation files(property('iastUtil17Jar'))
+  }
+}
+
+dependencies {
+  implementation group: 'org.springframework.boot', name: 'spring-boot-starter-web', version: '2.2.0.RELEASE'
+}
diff --git a/dd-smoke-tests/springboot-java-17/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/springboot-java-17/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/springboot-java-17/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/springboot-java-17/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/springboot-java-17/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/springboot-java-17/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/springboot-java-17/application/gradlew b/dd-smoke-tests/springboot-java-17/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/springboot-java-17/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/springboot-java-17/application/gradlew.bat b/dd-smoke-tests/springboot-java-17/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/springboot-java-17/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/springboot-java-17/application/settings.gradle b/dd-smoke-tests/springboot-java-17/application/settings.gradle
new file mode 100644
index 00000000000..e0193c924d2
--- /dev/null
+++ b/dd-smoke-tests/springboot-java-17/application/settings.gradle
@@ -0,0 +1,32 @@
+pluginManagement {
+  repositories {
+    mavenLocal()
+    if (settings.hasProperty("gradlePluginProxy")) {
+      maven {
+        url settings["gradlePluginProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    if (settings.hasProperty("mavenRepositoryProxy")) {
+      maven {
+        url settings["mavenRepositoryProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    gradlePluginPortal()
+    mavenCentral()
+  }
+}
+
+def isCI = providers.environmentVariable("CI").isPresent()
+
+if (isCI) {
+  def sharedRootDir = "$rootDir/../../../"
+  buildCache {
+    local {
+      directory = "$sharedRootDir/workspace/build-cache"
+    }
+  }
+}
+
+rootProject.name='springboot-java-17-smoketest'
diff --git a/dd-smoke-tests/springboot-java-17/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java b/dd-smoke-tests/springboot-java-17/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
similarity index 100%
rename from dd-smoke-tests/springboot-java-17/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
rename to dd-smoke-tests/springboot-java-17/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
diff --git a/dd-smoke-tests/springboot-java-17/build.gradle b/dd-smoke-tests/springboot-java-17/build.gradle
index cb878a92c7f..8db22c06133 100644
--- a/dd-smoke-tests/springboot-java-17/build.gradle
+++ b/dd-smoke-tests/springboot-java-17/build.gradle
@@ -1,42 +1,66 @@
-import org.springframework.boot.gradle.tasks.bundling.BootJar
-
-plugins {
-  id 'java'
-  id 'org.springframework.boot' version '2.7.15'
-  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
-  id 'java-test-fixtures'
-}
-
 apply from: "$rootDir/gradle/java.gradle"
 
+apply plugin: 'java-test-fixtures'
+
 testJvmConstraints {
   minJavaVersion = JavaVersion.VERSION_17
 }
 
-apply from: "$rootDir/gradle/spring-boot-plugin.gradle"
 description = 'SpringBoot Java 17 Smoke Tests.'
 
-dependencies {
-  implementation group: 'org.springframework.boot', name: 'spring-boot-starter-web', version: '2.2.0.RELEASE'
+def appDir = "$projectDir/application"
+def appBuildDir = "$buildDir/application"
+def isWindows = System.getProperty("os.name").toLowerCase().contains("win")
+def gradlewCommand = isWindows ? 'gradlew.bat' : 'gradlew'
 
-  testImplementation project(':dd-smoke-tests')
-  testImplementation testFixtures(project(":dd-smoke-tests:iast-util:iast-util-17"))
-  testImplementation testFixtures(project(':dd-smoke-tests:iast-util'))
+tasks.register('bootJar', Exec) {
+  workingDir appDir
+  environment += [
+    "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
+    "JAVA_HOME": getLazyJavaHomeFor(17)
+  ]
+  commandLine "$appDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir",
+    "-PiastUtil17Jar=${project(':dd-smoke-tests:iast-util:iast-util-17').tasks.jar.archiveFile.get()}"
+
+  outputs.cacheIf { true }
+
+  outputs.dir(appBuildDir)
+    .withPropertyName("applicationJar")
 
-  implementation project(':dd-smoke-tests:iast-util:iast-util-17')
+  inputs.files(fileTree(appDir) {
+    include '**/*'
+    exclude '.gradle/**'
+  })
+  .withPropertyName("application")
+  .withPathSensitivity(PathSensitivity.RELATIVE)
 }
 
-tasks.named("compileJava", JavaCompile) {
-  configureCompiler(it, 17, JavaVersion.VERSION_17)
+tasks.named('bootJar', Exec) {
+  dependsOn project(':dd-smoke-tests:iast-util:iast-util-17').tasks.named('jar')
+}
+
+dependencies {
+  testImplementation project(':dd-smoke-tests')
+  testImplementation testFixtures(project(":dd-smoke-tests:iast-util:iast-util-17"))
+  testImplementation testFixtures(project(':dd-smoke-tests:iast-util'))
 }
 
 tasks.withType(Test).configureEach {
-  dependsOn "bootJar"
-  def bootJarTask = tasks.named('bootJar', BootJar)
+  dependsOn 'bootJar'
   jvmArgumentProviders.add(new CommandLineArgumentProvider() {
       @Override
       Iterable<String> asArguments() {
-        return bootJarTask.map { ["-Ddatadog.smoketest.springboot.shadowJar.path=${it.archiveFile.get()}"] }.get()
+        return ["-Ddatadog.smoketest.springboot.shadowJar.path=$appBuildDir/libs/springboot-java-17-smoketest.jar"]
       }
     })
 }
+
+spotless {
+  java {
+    target "**/*.java"
+  }
+
+  groovyGradle {
+    target '*.gradle', "**/*.gradle"
+  }
+}
diff --git a/dd-smoke-tests/springboot-jetty-jsp/application/build.gradle b/dd-smoke-tests/springboot-jetty-jsp/application/build.gradle
new file mode 100644
index 00000000000..4c68c426f93
--- /dev/null
+++ b/dd-smoke-tests/springboot-jetty-jsp/application/build.gradle
@@ -0,0 +1,37 @@
+plugins {
+  id 'java'
+  id 'war'
+  id 'org.springframework.boot' version '2.7.15'
+  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
+}
+
+def sharedRootDir = "$rootDir/../../../"
+def sharedConfigDirectory = "$sharedRootDir/gradle"
+rootProject.ext.sharedConfigDirectory = sharedConfigDirectory
+
+apply from: "$sharedConfigDirectory/repositories.gradle"
+
+if (hasProperty('appBuildDir')) {
+  buildDir = property('appBuildDir')
+}
+
+version = ""
+
+java {
+  sourceCompatibility = '1.8'
+}
+
+sourceSets {
+  main {
+    resources.srcDir("src/main/webapp")
+  }
+}
+
+dependencies {
+  implementation 'org.springframework.boot:spring-boot-starter-web'
+
+  runtimeOnly("javax.servlet:jstl")
+  runtimeOnly("org.apache.tomcat.embed:tomcat-embed-jasper")
+
+  providedRuntime("org.springframework.boot:spring-boot-starter-jetty")
+}
diff --git a/dd-smoke-tests/springboot-jetty-jsp/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/springboot-jetty-jsp/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/springboot-jetty-jsp/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/springboot-jetty-jsp/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/springboot-jetty-jsp/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/springboot-jetty-jsp/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/springboot-jetty-jsp/application/gradlew b/dd-smoke-tests/springboot-jetty-jsp/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/springboot-jetty-jsp/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/springboot-jetty-jsp/application/gradlew.bat b/dd-smoke-tests/springboot-jetty-jsp/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/springboot-jetty-jsp/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/springboot-jetty-jsp/application/settings.gradle b/dd-smoke-tests/springboot-jetty-jsp/application/settings.gradle
new file mode 100644
index 00000000000..a2890a26aa3
--- /dev/null
+++ b/dd-smoke-tests/springboot-jetty-jsp/application/settings.gradle
@@ -0,0 +1,32 @@
+pluginManagement {
+  repositories {
+    mavenLocal()
+    if (settings.hasProperty("gradlePluginProxy")) {
+      maven {
+        url settings["gradlePluginProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    if (settings.hasProperty("mavenRepositoryProxy")) {
+      maven {
+        url settings["mavenRepositoryProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    gradlePluginPortal()
+    mavenCentral()
+  }
+}
+
+def isCI = providers.environmentVariable("CI").isPresent()
+
+if (isCI) {
+  def sharedRootDir = "$rootDir/../../../"
+  buildCache {
+    local {
+      directory = "$sharedRootDir/workspace/build-cache"
+    }
+  }
+}
+
+rootProject.name='springboot-jetty-jsp-smoketest'
diff --git a/dd-smoke-tests/springboot-jetty-jsp/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java b/dd-smoke-tests/springboot-jetty-jsp/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
similarity index 100%
rename from dd-smoke-tests/springboot-jetty-jsp/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
rename to dd-smoke-tests/springboot-jetty-jsp/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
diff --git a/dd-smoke-tests/springboot-jetty-jsp/src/main/java/datadog/smoketest/springboot/ViewController.java b/dd-smoke-tests/springboot-jetty-jsp/application/src/main/java/datadog/smoketest/springboot/ViewController.java
similarity index 100%
rename from dd-smoke-tests/springboot-jetty-jsp/src/main/java/datadog/smoketest/springboot/ViewController.java
rename to dd-smoke-tests/springboot-jetty-jsp/application/src/main/java/datadog/smoketest/springboot/ViewController.java
diff --git a/dd-smoke-tests/springboot-jetty-jsp/src/main/resources/application.properties b/dd-smoke-tests/springboot-jetty-jsp/application/src/main/resources/application.properties
similarity index 100%
rename from dd-smoke-tests/springboot-jetty-jsp/src/main/resources/application.properties
rename to dd-smoke-tests/springboot-jetty-jsp/application/src/main/resources/application.properties
diff --git a/dd-smoke-tests/springboot-jetty-jsp/src/main/webapp/WEB-INF/jsp/test_xss.jsp b/dd-smoke-tests/springboot-jetty-jsp/application/src/main/webapp/WEB-INF/jsp/test_xss.jsp
similarity index 100%
rename from dd-smoke-tests/springboot-jetty-jsp/src/main/webapp/WEB-INF/jsp/test_xss.jsp
rename to dd-smoke-tests/springboot-jetty-jsp/application/src/main/webapp/WEB-INF/jsp/test_xss.jsp
diff --git a/dd-smoke-tests/springboot-jetty-jsp/build.gradle b/dd-smoke-tests/springboot-jetty-jsp/build.gradle
index d8fdc4fbab4..612fbba25e6 100644
--- a/dd-smoke-tests/springboot-jetty-jsp/build.gradle
+++ b/dd-smoke-tests/springboot-jetty-jsp/build.gradle
@@ -1,47 +1,56 @@
-import org.springframework.boot.gradle.tasks.bundling.BootWar
-
-plugins {
-  id 'java'
-  id 'war'
-  id 'org.springframework.boot' version '2.7.15'
-  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
-  id 'java-test-fixtures'
-}
-
 apply from: "$rootDir/gradle/java.gradle"
-apply from: "$rootDir/gradle/spring-boot-plugin.gradle"
-description = 'SpringBoot Jetty JSP Smoke Tests.'
 
-java {
-  sourceCompatibility = '1.8'
-}
+apply plugin: 'java-test-fixtures'
 
-sourceSets {
-  main {
-    resources.srcDir("src/main/webapp")
-  }
+description = 'SpringBoot Jetty JSP Smoke Tests.'
+
+def appDir = "$projectDir/application"
+def appBuildDir = "$buildDir/application"
+def isWindows = System.getProperty("os.name").toLowerCase().contains("win")
+def gradlewCommand = isWindows ? 'gradlew.bat' : 'gradlew'
+
+tasks.register('bootWar', Exec) {
+  workingDir appDir
+  environment += [
+    "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
+    "JAVA_HOME": getLazyJavaHomeFor(8)
+  ]
+  commandLine "$appDir/${gradlewCommand}", "war", "bootWar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir"
+
+  outputs.cacheIf { true }
+
+  outputs.dir(appBuildDir)
+    .withPropertyName("applicationWar")
+
+  inputs.files(fileTree(appDir) {
+    include '**/*'
+    exclude '.gradle/**'
+  })
+  .withPropertyName("application")
+  .withPathSensitivity(PathSensitivity.RELATIVE)
 }
 
 dependencies {
-  implementation 'org.springframework.boot:spring-boot-starter-web'
-
-  runtimeOnly("javax.servlet:jstl")
-  runtimeOnly("org.apache.tomcat.embed:tomcat-embed-jasper")
-
-  providedRuntime("org.springframework.boot:spring-boot-starter-jetty")
-
   testImplementation project(':dd-smoke-tests')
   testImplementation(testFixtures(project(":dd-smoke-tests:iast-util")))
 }
 
 tasks.withType(Test).configureEach {
-  dependsOn "war", "bootWar"
-
+  dependsOn 'bootWar'
   jvmArgumentProviders.add(new CommandLineArgumentProvider() {
       @Override
       Iterable<String> asArguments() {
-        def bootWarTask = tasks.named('bootWar', BootWar).get()
-        return ["-Ddatadog.smoketest.springboot.war.path=${bootWarTask.archiveFile.get().getAsFile()}"]
+        return ["-Ddatadog.smoketest.springboot.war.path=$appBuildDir/libs/springboot-jetty-jsp-smoketest.war"]
       }
     })
 }
+
+spotless {
+  java {
+    target "**/*.java"
+  }
+
+  groovyGradle {
+    target '*.gradle', "**/*.gradle"
+  }
+}
diff --git a/dd-smoke-tests/springboot-jpa/application/build.gradle b/dd-smoke-tests/springboot-jpa/application/build.gradle
new file mode 100644
index 00000000000..a38bb884c1d
--- /dev/null
+++ b/dd-smoke-tests/springboot-jpa/application/build.gradle
@@ -0,0 +1,30 @@
+plugins {
+  id 'java'
+  id 'war'
+  id 'org.springframework.boot' version '2.6.0'
+}
+
+apply plugin: 'io.spring.dependency-management'
+
+def sharedRootDir = "$rootDir/../../../"
+def sharedConfigDirectory = "$sharedRootDir/gradle"
+rootProject.ext.sharedConfigDirectory = sharedConfigDirectory
+
+apply from: "$sharedConfigDirectory/repositories.gradle"
+
+if (hasProperty('appBuildDir')) {
+  buildDir = property('appBuildDir')
+}
+
+version = ""
+
+dependencies {
+  implementation 'org.springframework.boot:spring-boot-starter-web'
+  implementation 'org.springframework.boot:spring-boot-starter-data-jpa'
+  implementation 'org.apache.tomcat.embed:tomcat-embed-jasper'
+  implementation 'javax.servlet:jstl:1.2'
+  implementation 'com.h2database:h2:2.1.214'
+
+  compileOnly 'org.projectlombok:lombok:1.18.34'
+  annotationProcessor 'org.projectlombok:lombok:1.18.34'
+}
diff --git a/dd-smoke-tests/springboot-jpa/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/springboot-jpa/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/springboot-jpa/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/springboot-jpa/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/springboot-jpa/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/springboot-jpa/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/springboot-jpa/application/gradlew b/dd-smoke-tests/springboot-jpa/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/springboot-jpa/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/springboot-jpa/application/gradlew.bat b/dd-smoke-tests/springboot-jpa/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/springboot-jpa/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/springboot-jpa/application/settings.gradle b/dd-smoke-tests/springboot-jpa/application/settings.gradle
new file mode 100644
index 00000000000..6ba5b1b29bb
--- /dev/null
+++ b/dd-smoke-tests/springboot-jpa/application/settings.gradle
@@ -0,0 +1,32 @@
+pluginManagement {
+  repositories {
+    mavenLocal()
+    if (settings.hasProperty("gradlePluginProxy")) {
+      maven {
+        url settings["gradlePluginProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    if (settings.hasProperty("mavenRepositoryProxy")) {
+      maven {
+        url settings["mavenRepositoryProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    gradlePluginPortal()
+    mavenCentral()
+  }
+}
+
+def isCI = providers.environmentVariable("CI").isPresent()
+
+if (isCI) {
+  def sharedRootDir = "$rootDir/../../../"
+  buildCache {
+    local {
+      directory = "$sharedRootDir/workspace/build-cache"
+    }
+  }
+}
+
+rootProject.name='springboot-jpa-smoketest'
diff --git a/dd-smoke-tests/springboot-jpa/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java b/dd-smoke-tests/springboot-jpa/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
similarity index 100%
rename from dd-smoke-tests/springboot-jpa/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
rename to dd-smoke-tests/springboot-jpa/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
diff --git a/dd-smoke-tests/springboot-jpa/src/main/java/datadog/smoketest/springboot/controller/LibraryController.java b/dd-smoke-tests/springboot-jpa/application/src/main/java/datadog/smoketest/springboot/controller/LibraryController.java
similarity index 100%
rename from dd-smoke-tests/springboot-jpa/src/main/java/datadog/smoketest/springboot/controller/LibraryController.java
rename to dd-smoke-tests/springboot-jpa/application/src/main/java/datadog/smoketest/springboot/controller/LibraryController.java
diff --git a/dd-smoke-tests/springboot-jpa/src/main/java/datadog/smoketest/springboot/entity/Author.java b/dd-smoke-tests/springboot-jpa/application/src/main/java/datadog/smoketest/springboot/entity/Author.java
similarity index 100%
rename from dd-smoke-tests/springboot-jpa/src/main/java/datadog/smoketest/springboot/entity/Author.java
rename to dd-smoke-tests/springboot-jpa/application/src/main/java/datadog/smoketest/springboot/entity/Author.java
diff --git a/dd-smoke-tests/springboot-jpa/src/main/java/datadog/smoketest/springboot/entity/Book.java b/dd-smoke-tests/springboot-jpa/application/src/main/java/datadog/smoketest/springboot/entity/Book.java
similarity index 100%
rename from dd-smoke-tests/springboot-jpa/src/main/java/datadog/smoketest/springboot/entity/Book.java
rename to dd-smoke-tests/springboot-jpa/application/src/main/java/datadog/smoketest/springboot/entity/Book.java
diff --git a/dd-smoke-tests/springboot-jpa/src/main/java/datadog/smoketest/springboot/entity/Library.java b/dd-smoke-tests/springboot-jpa/application/src/main/java/datadog/smoketest/springboot/entity/Library.java
similarity index 100%
rename from dd-smoke-tests/springboot-jpa/src/main/java/datadog/smoketest/springboot/entity/Library.java
rename to dd-smoke-tests/springboot-jpa/application/src/main/java/datadog/smoketest/springboot/entity/Library.java
diff --git a/dd-smoke-tests/springboot-jpa/src/main/java/datadog/smoketest/springboot/entity/Owner.java b/dd-smoke-tests/springboot-jpa/application/src/main/java/datadog/smoketest/springboot/entity/Owner.java
similarity index 100%
rename from dd-smoke-tests/springboot-jpa/src/main/java/datadog/smoketest/springboot/entity/Owner.java
rename to dd-smoke-tests/springboot-jpa/application/src/main/java/datadog/smoketest/springboot/entity/Owner.java
diff --git a/dd-smoke-tests/springboot-jpa/src/main/java/datadog/smoketest/springboot/filter/SessionVisitorFilter.java b/dd-smoke-tests/springboot-jpa/application/src/main/java/datadog/smoketest/springboot/filter/SessionVisitorFilter.java
similarity index 100%
rename from dd-smoke-tests/springboot-jpa/src/main/java/datadog/smoketest/springboot/filter/SessionVisitorFilter.java
rename to dd-smoke-tests/springboot-jpa/application/src/main/java/datadog/smoketest/springboot/filter/SessionVisitorFilter.java
diff --git a/dd-smoke-tests/springboot-jpa/src/main/java/datadog/smoketest/springboot/service/LibraryService.java b/dd-smoke-tests/springboot-jpa/application/src/main/java/datadog/smoketest/springboot/service/LibraryService.java
similarity index 100%
rename from dd-smoke-tests/springboot-jpa/src/main/java/datadog/smoketest/springboot/service/LibraryService.java
rename to dd-smoke-tests/springboot-jpa/application/src/main/java/datadog/smoketest/springboot/service/LibraryService.java
diff --git a/dd-smoke-tests/springboot-jpa/src/main/resources/application.yml b/dd-smoke-tests/springboot-jpa/application/src/main/resources/application.yml
similarity index 100%
rename from dd-smoke-tests/springboot-jpa/src/main/resources/application.yml
rename to dd-smoke-tests/springboot-jpa/application/src/main/resources/application.yml
diff --git a/dd-smoke-tests/springboot-jpa/src/main/webapp/WEB-INF/jsp/update.jsp b/dd-smoke-tests/springboot-jpa/application/src/main/webapp/WEB-INF/jsp/update.jsp
similarity index 100%
rename from dd-smoke-tests/springboot-jpa/src/main/webapp/WEB-INF/jsp/update.jsp
rename to dd-smoke-tests/springboot-jpa/application/src/main/webapp/WEB-INF/jsp/update.jsp
diff --git a/dd-smoke-tests/springboot-jpa/build.gradle b/dd-smoke-tests/springboot-jpa/build.gradle
index af9c22ff235..6c2470801cb 100644
--- a/dd-smoke-tests/springboot-jpa/build.gradle
+++ b/dd-smoke-tests/springboot-jpa/build.gradle
@@ -1,40 +1,43 @@
-import org.springframework.boot.gradle.tasks.bundling.BootWar
-
-plugins {
-  id 'java'
-  id 'war'
-  id 'org.springframework.boot' version '2.6.0'
-}
-
-apply plugin: 'io.spring.dependency-management'
 apply from: "$rootDir/gradle/java.gradle"
-apply from: "$rootDir/gradle/spring-boot-plugin.gradle"
+
 description = 'SpringBoot JPA Smoke Tests.'
 
-dependencies {
-  implementation 'org.springframework.boot:spring-boot-starter-web'
-  implementation 'org.springframework.boot:spring-boot-starter-data-jpa'
-  implementation 'org.apache.tomcat.embed:tomcat-embed-jasper'
-  implementation 'javax.servlet:jstl:1.2'
-  implementation 'com.h2database:h2:2.1.214'
+def appDir = "$projectDir/application"
+def appBuildDir = "$buildDir/application"
+def isWindows = System.getProperty("os.name").toLowerCase().contains("win")
+def gradlewCommand = isWindows ? 'gradlew.bat' : 'gradlew'
+
+tasks.register('bootWar', Exec) {
+  workingDir appDir
+  environment += [
+    "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
+    "JAVA_HOME": getLazyJavaHomeFor(8)
+  ]
+  commandLine "$appDir/${gradlewCommand}", "bootWar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir"
+
+  outputs.cacheIf { true }
+
+  outputs.dir(appBuildDir)
+    .withPropertyName("applicationWar")
+
+  inputs.files(fileTree(appDir) {
+    include '**/*'
+    exclude '.gradle/**'
+  })
+  .withPropertyName("application")
+  .withPathSensitivity(PathSensitivity.RELATIVE)
+}
 
+dependencies {
   testImplementation project(':dd-smoke-tests')
-
-  compileOnly 'org.projectlombok:lombok:1.18.34'
-  annotationProcessor 'org.projectlombok:lombok:1.18.34'
-
-  testCompileOnly 'org.projectlombok:lombok:1.18.34'
-  testAnnotationProcessor 'org.projectlombok:lombok:1.18.34'
 }
 
 tasks.withType(Test).configureEach {
-  dependsOn "bootWar"
-
+  dependsOn 'bootWar'
   jvmArgumentProviders.add(new CommandLineArgumentProvider() {
       @Override
       Iterable<String> asArguments() {
-        def bootWarTask = tasks.named('bootWar', BootWar).get()
-        return ["-Ddatadog.smoketest.springboot.bootWar.path=${bootWarTask.archiveFile.get()}"]
+        return ["-Ddatadog.smoketest.springboot.bootWar.path=$appBuildDir/libs/springboot-jpa-smoketest.war"]
       }
     })
 }
@@ -42,3 +45,13 @@ tasks.withType(Test).configureEach {
 tasks.withType(GroovyCompile).configureEach {
   configureCompiler(it, 8)
 }
+
+spotless {
+  java {
+    target "**/*.java"
+  }
+
+  groovyGradle {
+    target '*.gradle', "**/*.gradle"
+  }
+}
diff --git a/dd-smoke-tests/springboot-thymeleaf/application/build.gradle b/dd-smoke-tests/springboot-thymeleaf/application/build.gradle
new file mode 100644
index 00000000000..77f8e57d848
--- /dev/null
+++ b/dd-smoke-tests/springboot-thymeleaf/application/build.gradle
@@ -0,0 +1,26 @@
+plugins {
+  id 'java'
+  id 'org.springframework.boot' version '2.7.15'
+  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
+}
+
+def sharedRootDir = "$rootDir/../../../"
+def sharedConfigDirectory = "$sharedRootDir/gradle"
+rootProject.ext.sharedConfigDirectory = sharedConfigDirectory
+
+apply from: "$sharedConfigDirectory/repositories.gradle"
+
+if (hasProperty('appBuildDir')) {
+  buildDir = property('appBuildDir')
+}
+
+version = ""
+
+java {
+  sourceCompatibility = '1.8'
+}
+
+dependencies {
+  implementation 'org.springframework.boot:spring-boot-starter-web'
+  implementation 'org.springframework.boot:spring-boot-starter-thymeleaf'
+}
diff --git a/dd-smoke-tests/springboot-thymeleaf/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/springboot-thymeleaf/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/springboot-thymeleaf/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/springboot-thymeleaf/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/springboot-thymeleaf/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/springboot-thymeleaf/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/springboot-thymeleaf/application/gradlew b/dd-smoke-tests/springboot-thymeleaf/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/springboot-thymeleaf/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/springboot-thymeleaf/application/gradlew.bat b/dd-smoke-tests/springboot-thymeleaf/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/springboot-thymeleaf/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/springboot-thymeleaf/application/settings.gradle b/dd-smoke-tests/springboot-thymeleaf/application/settings.gradle
new file mode 100644
index 00000000000..ab2f4d42f90
--- /dev/null
+++ b/dd-smoke-tests/springboot-thymeleaf/application/settings.gradle
@@ -0,0 +1,32 @@
+pluginManagement {
+  repositories {
+    mavenLocal()
+    if (settings.hasProperty("gradlePluginProxy")) {
+      maven {
+        url settings["gradlePluginProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    if (settings.hasProperty("mavenRepositoryProxy")) {
+      maven {
+        url settings["mavenRepositoryProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    gradlePluginPortal()
+    mavenCentral()
+  }
+}
+
+def isCI = providers.environmentVariable("CI").isPresent()
+
+if (isCI) {
+  def sharedRootDir = "$rootDir/../../../"
+  buildCache {
+    local {
+      directory = "$sharedRootDir/workspace/build-cache"
+    }
+  }
+}
+
+rootProject.name='springboot-thymeleaf-smoketest'
diff --git a/dd-smoke-tests/springboot-thymeleaf/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java b/dd-smoke-tests/springboot-thymeleaf/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
similarity index 100%
rename from dd-smoke-tests/springboot-thymeleaf/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
rename to dd-smoke-tests/springboot-thymeleaf/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
diff --git a/dd-smoke-tests/springboot-thymeleaf/src/main/java/datadog/smoketest/springboot/XssController.java b/dd-smoke-tests/springboot-thymeleaf/application/src/main/java/datadog/smoketest/springboot/XssController.java
similarity index 100%
rename from dd-smoke-tests/springboot-thymeleaf/src/main/java/datadog/smoketest/springboot/XssController.java
rename to dd-smoke-tests/springboot-thymeleaf/application/src/main/java/datadog/smoketest/springboot/XssController.java
diff --git a/dd-smoke-tests/springboot-thymeleaf/src/main/resources/templates/utext.html b/dd-smoke-tests/springboot-thymeleaf/application/src/main/resources/templates/utext.html
similarity index 100%
rename from dd-smoke-tests/springboot-thymeleaf/src/main/resources/templates/utext.html
rename to dd-smoke-tests/springboot-thymeleaf/application/src/main/resources/templates/utext.html
diff --git a/dd-smoke-tests/springboot-thymeleaf/build.gradle b/dd-smoke-tests/springboot-thymeleaf/build.gradle
index 7de0a0833e5..0389460b668 100644
--- a/dd-smoke-tests/springboot-thymeleaf/build.gradle
+++ b/dd-smoke-tests/springboot-thymeleaf/build.gradle
@@ -1,35 +1,58 @@
-import org.springframework.boot.gradle.tasks.bundling.BootJar
+apply from: "$rootDir/gradle/java.gradle"
 
-plugins {
-  id 'java'
-  id 'org.springframework.boot' version '2.7.15'
-  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
-  id 'java-test-fixtures'
-}
+apply plugin: 'java-test-fixtures'
 
-apply from: "$rootDir/gradle/java.gradle"
-apply from: "$rootDir/gradle/spring-boot-plugin.gradle"
 description = 'SpringBoot thymeleaf 3 Smoke Tests.'
 
-java {
-  sourceCompatibility = '1.8'
+def appDir = "$projectDir/application"
+def appBuildDir = "$buildDir/application"
+def isWindows = System.getProperty("os.name").toLowerCase().contains("win")
+def gradlewCommand = isWindows ? 'gradlew.bat' : 'gradlew'
+
+tasks.register('bootJar', Exec) {
+  workingDir appDir
+  environment += [
+    "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
+    "JAVA_HOME": getLazyJavaHomeFor(8)
+  ]
+  commandLine "$appDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir"
+
+  outputs.cacheIf { true }
+
+  outputs.dir(appBuildDir)
+    .withPropertyName("applicationJar")
+
+  inputs.files(fileTree(appDir) {
+    include '**/*'
+    exclude '.gradle/**'
+  })
+  .withPropertyName("application")
+  .withPathSensitivity(PathSensitivity.RELATIVE)
 }
 
 dependencies {
-  implementation 'org.springframework.boot:spring-boot-starter-web'
-  implementation 'org.springframework.boot:spring-boot-starter-thymeleaf'
-
   testImplementation project(':dd-smoke-tests')
   testImplementation(testFixtures(project(":dd-smoke-tests:iast-util")))
 }
 
 tasks.withType(Test).configureEach {
-  dependsOn "bootJar"
-  def bootJarTask = tasks.named('bootJar', BootJar)
+  dependsOn 'bootJar'
   jvmArgumentProviders.add(new CommandLineArgumentProvider() {
       @Override
       Iterable<String> asArguments() {
-        return bootJarTask.map { ["-Ddatadog.smoketest.springboot.shadowJar.path=${it.archiveFile.get()}"] }.get()
+        return [
+          "-Ddatadog.smoketest.springboot.shadowJar.path=$appBuildDir/libs/springboot-thymeleaf-smoketest.jar"
+        ]
       }
     })
 }
+
+spotless {
+  java {
+    target "**/*.java"
+  }
+
+  groovyGradle {
+    target '*.gradle', "**/*.gradle"
+  }
+}
diff --git a/dd-smoke-tests/springboot-tomcat-jsp/application/build.gradle b/dd-smoke-tests/springboot-tomcat-jsp/application/build.gradle
new file mode 100644
index 00000000000..8632e7afc64
--- /dev/null
+++ b/dd-smoke-tests/springboot-tomcat-jsp/application/build.gradle
@@ -0,0 +1,37 @@
+plugins {
+  id 'java'
+  id 'war'
+  id 'org.springframework.boot' version '2.7.15'
+  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
+}
+
+def sharedRootDir = "$rootDir/../../../"
+def sharedConfigDirectory = "$sharedRootDir/gradle"
+rootProject.ext.sharedConfigDirectory = sharedConfigDirectory
+
+apply from: "$sharedConfigDirectory/repositories.gradle"
+
+if (hasProperty('appBuildDir')) {
+  buildDir = property('appBuildDir')
+}
+
+version = ""
+
+java {
+  sourceCompatibility = '1.8'
+}
+
+sourceSets {
+  main {
+    resources.srcDir("src/main/webapp")
+  }
+}
+
+dependencies {
+  implementation 'org.springframework.boot:spring-boot-starter-web'
+
+  runtimeOnly("javax.servlet:jstl")
+  runtimeOnly("org.apache.tomcat.embed:tomcat-embed-jasper")
+
+  providedRuntime("org.springframework.boot:spring-boot-starter-tomcat")
+}
diff --git a/dd-smoke-tests/springboot-tomcat-jsp/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/springboot-tomcat-jsp/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/springboot-tomcat-jsp/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/springboot-tomcat-jsp/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/springboot-tomcat-jsp/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/springboot-tomcat-jsp/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/springboot-tomcat-jsp/application/gradlew b/dd-smoke-tests/springboot-tomcat-jsp/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/springboot-tomcat-jsp/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/springboot-tomcat-jsp/application/gradlew.bat b/dd-smoke-tests/springboot-tomcat-jsp/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/springboot-tomcat-jsp/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/springboot-tomcat-jsp/application/settings.gradle b/dd-smoke-tests/springboot-tomcat-jsp/application/settings.gradle
new file mode 100644
index 00000000000..bb366810698
--- /dev/null
+++ b/dd-smoke-tests/springboot-tomcat-jsp/application/settings.gradle
@@ -0,0 +1,32 @@
+pluginManagement {
+  repositories {
+    mavenLocal()
+    if (settings.hasProperty("gradlePluginProxy")) {
+      maven {
+        url settings["gradlePluginProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    if (settings.hasProperty("mavenRepositoryProxy")) {
+      maven {
+        url settings["mavenRepositoryProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    gradlePluginPortal()
+    mavenCentral()
+  }
+}
+
+def isCI = providers.environmentVariable("CI").isPresent()
+
+if (isCI) {
+  def sharedRootDir = "$rootDir/../../../"
+  buildCache {
+    local {
+      directory = "$sharedRootDir/workspace/build-cache"
+    }
+  }
+}
+
+rootProject.name='springboot-tomcat-jsp-smoketest'
diff --git a/dd-smoke-tests/springboot-tomcat-jsp/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java b/dd-smoke-tests/springboot-tomcat-jsp/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
similarity index 100%
rename from dd-smoke-tests/springboot-tomcat-jsp/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
rename to dd-smoke-tests/springboot-tomcat-jsp/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
diff --git a/dd-smoke-tests/springboot-tomcat-jsp/src/main/java/datadog/smoketest/springboot/ViewController.java b/dd-smoke-tests/springboot-tomcat-jsp/application/src/main/java/datadog/smoketest/springboot/ViewController.java
similarity index 100%
rename from dd-smoke-tests/springboot-tomcat-jsp/src/main/java/datadog/smoketest/springboot/ViewController.java
rename to dd-smoke-tests/springboot-tomcat-jsp/application/src/main/java/datadog/smoketest/springboot/ViewController.java
diff --git a/dd-smoke-tests/springboot-tomcat-jsp/src/main/resources/application.properties b/dd-smoke-tests/springboot-tomcat-jsp/application/src/main/resources/application.properties
similarity index 100%
rename from dd-smoke-tests/springboot-tomcat-jsp/src/main/resources/application.properties
rename to dd-smoke-tests/springboot-tomcat-jsp/application/src/main/resources/application.properties
diff --git a/dd-smoke-tests/springboot-tomcat-jsp/src/main/webapp/WEB-INF/jsp/test_xss.jsp b/dd-smoke-tests/springboot-tomcat-jsp/application/src/main/webapp/WEB-INF/jsp/test_xss.jsp
similarity index 100%
rename from dd-smoke-tests/springboot-tomcat-jsp/src/main/webapp/WEB-INF/jsp/test_xss.jsp
rename to dd-smoke-tests/springboot-tomcat-jsp/application/src/main/webapp/WEB-INF/jsp/test_xss.jsp
diff --git a/dd-smoke-tests/springboot-tomcat-jsp/build.gradle b/dd-smoke-tests/springboot-tomcat-jsp/build.gradle
index 224274ece2a..1e2af9ea717 100644
--- a/dd-smoke-tests/springboot-tomcat-jsp/build.gradle
+++ b/dd-smoke-tests/springboot-tomcat-jsp/build.gradle
@@ -1,47 +1,56 @@
-import org.springframework.boot.gradle.tasks.bundling.BootWar
-
-plugins {
-  id 'java'
-  id 'war'
-  id 'org.springframework.boot' version '2.7.15'
-  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
-  id 'java-test-fixtures'
-}
-
 apply from: "$rootDir/gradle/java.gradle"
-apply from: "$rootDir/gradle/spring-boot-plugin.gradle"
-description = 'SpringBoot Tomcat JSP Smoke Tests.'
 
-java {
-  sourceCompatibility = '1.8'
-}
+apply plugin: 'java-test-fixtures'
 
-sourceSets {
-  main {
-    resources.srcDir("src/main/webapp")
-  }
+description = 'SpringBoot Tomcat JSP Smoke Tests.'
+
+def appDir = "$projectDir/application"
+def appBuildDir = "$buildDir/application"
+def isWindows = System.getProperty("os.name").toLowerCase().contains("win")
+def gradlewCommand = isWindows ? 'gradlew.bat' : 'gradlew'
+
+tasks.register('bootWar', Exec) {
+  workingDir appDir
+  environment += [
+    "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
+    "JAVA_HOME": getLazyJavaHomeFor(8)
+  ]
+  commandLine "$appDir/${gradlewCommand}", "war", "bootWar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir"
+
+  outputs.cacheIf { true }
+
+  outputs.dir(appBuildDir)
+    .withPropertyName("applicationWar")
+
+  inputs.files(fileTree(appDir) {
+    include '**/*'
+    exclude '.gradle/**'
+  })
+  .withPropertyName("application")
+  .withPathSensitivity(PathSensitivity.RELATIVE)
 }
 
 dependencies {
-  implementation 'org.springframework.boot:spring-boot-starter-web'
-
-  runtimeOnly("javax.servlet:jstl")
-  runtimeOnly("org.apache.tomcat.embed:tomcat-embed-jasper")
-
-  providedRuntime("org.springframework.boot:spring-boot-starter-tomcat")
-
   testImplementation project(':dd-smoke-tests')
   testImplementation(testFixtures(project(":dd-smoke-tests:iast-util")))
 }
 
 tasks.withType(Test).configureEach {
-  dependsOn "war", "bootWar"
-
+  dependsOn 'bootWar'
   jvmArgumentProviders.add(new CommandLineArgumentProvider() {
       @Override
       Iterable<String> asArguments() {
-        def bootWarTask = tasks.named('bootWar', BootWar).get()
-        return ["-Ddatadog.smoketest.springboot.war.path=${bootWarTask.archiveFile.get().getAsFile()}"]
+        return ["-Ddatadog.smoketest.springboot.war.path=$appBuildDir/libs/springboot-tomcat-jsp-smoketest.war"]
       }
     })
 }
+
+spotless {
+  java {
+    target "**/*.java"
+  }
+
+  groovyGradle {
+    target '*.gradle', "**/*.gradle"
+  }
+}
diff --git a/dd-smoke-tests/springboot-tomcat/application/build.gradle b/dd-smoke-tests/springboot-tomcat/application/build.gradle
new file mode 100644
index 00000000000..5d1b73a7518
--- /dev/null
+++ b/dd-smoke-tests/springboot-tomcat/application/build.gradle
@@ -0,0 +1,83 @@
+plugins {
+  id 'war'
+  id 'org.springframework.boot' version '2.5.12'
+}
+
+def sharedRootDir = "$rootDir/../../../"
+def sharedConfigDirectory = "$sharedRootDir/gradle"
+rootProject.ext.sharedConfigDirectory = sharedConfigDirectory
+
+apply from: "$sharedConfigDirectory/repositories.gradle"
+
+if (hasProperty('appBuildDir')) {
+  buildDir = property('appBuildDir')
+}
+
+version = ""
+
+ext {
+  serverName = 'tomcat'
+  serverModule = 'tomcat-9'
+  serverVersion = '9.0.117'
+  serverExtension = 'zip'
+}
+
+repositories {
+  ivy {
+    url = 'https://dlcdn.apache.org'
+    patternLayout {
+      artifact '/[organisation]/[module]/v[revision]/bin/apache-[organisation]-[revision].[ext]'
+    }
+    metadataSources {
+      it.artifact()
+    }
+  }
+}
+
+configurations {
+  serverFile {
+    extendsFrom implementation
+    canBeResolved = true
+  }
+}
+
+dependencies {
+  // uses the ivy repository url to download the tomcat server
+  // organisation = serverName, revision = serverVersion, module = serverModule, ext = serverExtension
+  serverFile "${serverName}:${serverModule}:${serverVersion}@${serverExtension}"
+
+  implementation group: 'org.springframework.boot', name: 'spring-boot-starter-web', version: '2.5.12'
+  providedRuntime group: 'org.springframework.boot', name: 'spring-boot-starter-tomcat', version: '2.5.12'
+}
+
+tasks.register("unzip", Copy) {
+  def zipFileNamePrefix = "tomcat"
+  def serverZipTree = providers.provider {
+    // eager access
+    def zipPath = project.configurations.serverFile.find {
+      it.name.startsWith(zipFileNamePrefix)
+    }
+    if (zipPath == null) {
+      throw new GradleException("Can't find server zip file that starts with: " + zipFileNamePrefix)
+    }
+    zipTree(zipPath)
+  }
+
+  from serverZipTree
+  into layout.buildDirectory
+
+  // When tests are disabled this would still be run, so disable this manually
+  onlyIf { !project.rootProject.hasProperty("skipTests") }
+}
+
+tasks.named('bootWar') {
+  dependsOn 'unzip'
+}
+
+tasks.named('bootWarMainClassName') {
+  dependsOn 'unzip'
+}
+
+tasks.named('war') {
+  dependsOn 'unzip'
+}
diff --git a/dd-smoke-tests/springboot-tomcat/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/springboot-tomcat/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/springboot-tomcat/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/springboot-tomcat/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/springboot-tomcat/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/springboot-tomcat/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/springboot-tomcat/application/gradlew b/dd-smoke-tests/springboot-tomcat/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/springboot-tomcat/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/springboot-tomcat/application/gradlew.bat b/dd-smoke-tests/springboot-tomcat/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/springboot-tomcat/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/springboot-tomcat/application/settings.gradle b/dd-smoke-tests/springboot-tomcat/application/settings.gradle
new file mode 100644
index 00000000000..ae63395506c
--- /dev/null
+++ b/dd-smoke-tests/springboot-tomcat/application/settings.gradle
@@ -0,0 +1,32 @@
+pluginManagement {
+  repositories {
+    mavenLocal()
+    if (settings.hasProperty("gradlePluginProxy")) {
+      maven {
+        url settings["gradlePluginProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    if (settings.hasProperty("mavenRepositoryProxy")) {
+      maven {
+        url settings["mavenRepositoryProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    gradlePluginPortal()
+    mavenCentral()
+  }
+}
+
+def isCI = providers.environmentVariable("CI").isPresent()
+
+if (isCI) {
+  def sharedRootDir = "$rootDir/../../../"
+  buildCache {
+    local {
+      directory = "$sharedRootDir/workspace/build-cache"
+    }
+  }
+}
+
+rootProject.name='springboot-tomcat-smoketest'
diff --git a/dd-smoke-tests/springboot-tomcat/src/main/java/datadog/smoketest/springboot/SpringbootTomcatApplication.java b/dd-smoke-tests/springboot-tomcat/application/src/main/java/datadog/smoketest/springboot/SpringbootTomcatApplication.java
similarity index 100%
rename from dd-smoke-tests/springboot-tomcat/src/main/java/datadog/smoketest/springboot/SpringbootTomcatApplication.java
rename to dd-smoke-tests/springboot-tomcat/application/src/main/java/datadog/smoketest/springboot/SpringbootTomcatApplication.java
diff --git a/dd-smoke-tests/springboot-tomcat/src/main/java/datadog/smoketest/springboot/controller/TestSuite.java b/dd-smoke-tests/springboot-tomcat/application/src/main/java/datadog/smoketest/springboot/controller/TestSuite.java
similarity index 100%
rename from dd-smoke-tests/springboot-tomcat/src/main/java/datadog/smoketest/springboot/controller/TestSuite.java
rename to dd-smoke-tests/springboot-tomcat/application/src/main/java/datadog/smoketest/springboot/controller/TestSuite.java
diff --git a/dd-smoke-tests/springboot-tomcat/src/main/java/datadog/smoketest/springboot/controller/ViewController.java b/dd-smoke-tests/springboot-tomcat/application/src/main/java/datadog/smoketest/springboot/controller/ViewController.java
similarity index 100%
rename from dd-smoke-tests/springboot-tomcat/src/main/java/datadog/smoketest/springboot/controller/ViewController.java
rename to dd-smoke-tests/springboot-tomcat/application/src/main/java/datadog/smoketest/springboot/controller/ViewController.java
diff --git a/dd-smoke-tests/springboot-tomcat/src/main/resources/application.properties b/dd-smoke-tests/springboot-tomcat/application/src/main/resources/application.properties
similarity index 100%
rename from dd-smoke-tests/springboot-tomcat/src/main/resources/application.properties
rename to dd-smoke-tests/springboot-tomcat/application/src/main/resources/application.properties
diff --git a/dd-smoke-tests/springboot-tomcat/build.gradle b/dd-smoke-tests/springboot-tomcat/build.gradle
index 14d0705eeca..a3968b48a23 100644
--- a/dd-smoke-tests/springboot-tomcat/build.gradle
+++ b/dd-smoke-tests/springboot-tomcat/build.gradle
@@ -1,126 +1,60 @@
-import org.springframework.boot.gradle.tasks.bundling.BootWar
-
-plugins {
-  id 'war'
-  id 'org.springframework.boot' version '2.5.12'
-}
-
-ext {
-  serverName = 'tomcat'
-  serverModule = 'tomcat-9'
-  serverVersion = '9.0.117'
-  serverExtension = 'zip'
-}
-
 apply from: "$rootDir/gradle/java.gradle"
-apply from: "$rootDir/gradle/spring-boot-plugin.gradle"
-description = 'SpringBoot Tomcat Smoke Tests.'
 
-repositories {
-  ivy {
-    url = 'https://dlcdn.apache.org'
-    patternLayout {
-      artifact '/[organisation]/[module]/v[revision]/bin/apache-[organisation]-[revision].[ext]'
-    }
-    metadataSources {
-      it.artifact()
-    }
-  }
-}
+description = 'SpringBoot Tomcat Smoke Tests.'
 
-configurations {
-  serverFile {
-    extendsFrom implementation
-    canBeResolved = true
-  }
-}
+def appDir = "$projectDir/application"
+def appBuildDir = "$buildDir/application"
+def isWindows = System.getProperty("os.name").toLowerCase().contains("win")
+def gradlewCommand = isWindows ? 'gradlew.bat' : 'gradlew'
 
-dependencies {
-  // uses the ivy repository url to download the tomcat server
-  // organisation = serverName, revision = serverVersion, module = serverModule, ext = serverExtension
-  serverFile "${serverName}:${serverModule}:${serverVersion}@${serverExtension}"
+def serverName = 'tomcat'
+def serverVersion = '9.0.117'
 
-  testImplementation project(':dd-smoke-tests')
-}
+tasks.register('bootWar', Exec) {
+  workingDir appDir
+  environment += [
+    "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
+    "JAVA_HOME": getLazyJavaHomeFor(8)
+  ]
+  commandLine "$appDir/${gradlewCommand}", "bootWar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir"
 
-tasks.register("unzip", Copy) {
-  def zipFileNamePrefix = "tomcat"
-  def serverZipTree = providers.provider {
-    // eager access
-    def zipPath = project.configurations.serverFile.find {
-      it.name.startsWith(zipFileNamePrefix)
-    }
-    if (zipPath == null) {
-      throw new GradleException("Can't find server zip file that starts with: " + zipFileNamePrefix)
-    }
-    zipTree(zipPath)
-  }
+  outputs.cacheIf { true }
 
-  from serverZipTree
-  into layout.buildDirectory
+  outputs.dir(appBuildDir)
+    .withPropertyName("applicationWar")
 
-  // When tests are disabled this would still be run, so disable this manually
-  onlyIf { !project.rootProject.hasProperty("skipTests") }
+  inputs.files(fileTree(appDir) {
+    include '**/*'
+    exclude '.gradle/**'
+  })
+  .withPropertyName("application")
+  .withPathSensitivity(PathSensitivity.RELATIVE)
 }
 
 dependencies {
-  implementation group: 'org.springframework.boot', name: 'spring-boot-starter-web', version: '2.5.12'
-  providedRuntime group: 'org.springframework.boot', name: 'spring-boot-starter-tomcat', version: '2.5.12'
-  testImplementation group: 'commons-io', name: 'commons-io', version: '2.11.0'
   testImplementation project(':dd-smoke-tests')
-}
-
-tasks.named('sourcesJar') {
-  dependsOn 'unzip'
-}
-
-tasks.named('javadocJar') {
-  dependsOn 'unzip'
-}
-
-tasks.named('bootWar') {
-  dependsOn 'unzip'
-}
-
-tasks.named('bootWarMainClassName') {
-  dependsOn 'unzip'
-}
-
-tasks.named('war') {
-  dependsOn 'unzip'
-}
-
-tasks.named('javadocJar') {
-  dependsOn 'unzip'
-}
-
-tasks.named('sourcesJar') {
-  dependsOn 'unzip'
-}
-
-tasks.named('forbiddenApisMain') {
-  dependsOn 'unzip'
-}
-
-tasks.named('spotbugsMain') {
-  dependsOn 'unzip'
-}
-
-tasks.matching({it.name.startsWith('compileTest')}).configureEach {
-  dependsOn 'war', 'bootWar', 'unzip'
+  testImplementation group: 'commons-io', name: 'commons-io', version: '2.11.0'
 }
 
 tasks.withType(Test).configureEach {
-  dependsOn "war", "bootWar", "unzip"
-
+  dependsOn 'bootWar'
   jvmArgumentProviders.add(new CommandLineArgumentProvider() {
       @Override
       Iterable<String> asArguments() {
-        def bootWarTask = tasks.named('bootWar', BootWar).get()
         return [
-          "-Ddatadog.smoketest.springboot.war.path=${bootWarTask.archiveFile.get().getAsFile()}",
-          "-Ddatadog.smoketest.tomcatDir=${layout.buildDirectory.get()}/apache-${serverName}-${serverVersion}"
+          "-Ddatadog.smoketest.springboot.war.path=$appBuildDir/libs/springboot-tomcat-smoketest.war",
+          "-Ddatadog.smoketest.tomcatDir=$appBuildDir/apache-${serverName}-${serverVersion}"
         ]
       }
     })
 }
+
+spotless {
+  java {
+    target "**/*.java"
+  }
+
+  groovyGradle {
+    target '*.gradle', "**/*.gradle"
+  }
+}
diff --git a/dd-smoke-tests/springboot-velocity/application/build.gradle b/dd-smoke-tests/springboot-velocity/application/build.gradle
new file mode 100644
index 00000000000..49a85dacc10
--- /dev/null
+++ b/dd-smoke-tests/springboot-velocity/application/build.gradle
@@ -0,0 +1,25 @@
+plugins {
+  id 'java'
+  id 'org.springframework.boot' version '2.7.15'
+  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
+}
+
+def sharedRootDir = "$rootDir/../../../"
+def sharedConfigDirectory = "$sharedRootDir/gradle"
+rootProject.ext.sharedConfigDirectory = sharedConfigDirectory
+
+apply from: "$sharedConfigDirectory/repositories.gradle"
+
+if (hasProperty('appBuildDir')) {
+  buildDir = property('appBuildDir')
+}
+
+version = ""
+
+dependencies {
+  implementation group: 'org.springframework.boot', name: 'spring-boot-starter-web', version: '1.5.18.RELEASE'
+  implementation group: 'org.apache.velocity', name: 'velocity', version: '1.5'
+  implementation(group: 'org.apache.velocity', name: 'velocity-tools', version: '1.3') {
+    exclude group: 'javax.servlet', module: 'servlet-api'
+  }
+}
diff --git a/dd-smoke-tests/springboot-velocity/application/gradle/wrapper/gradle-wrapper.jar b/dd-smoke-tests/springboot-velocity/application/gradle/wrapper/gradle-wrapper.jar
new file mode 100644
index 00000000000..e708b1c023e
Binary files /dev/null and b/dd-smoke-tests/springboot-velocity/application/gradle/wrapper/gradle-wrapper.jar differ
diff --git a/dd-smoke-tests/springboot-velocity/application/gradle/wrapper/gradle-wrapper.properties b/dd-smoke-tests/springboot-velocity/application/gradle/wrapper/gradle-wrapper.properties
new file mode 100644
index 00000000000..a4cf193f638
--- /dev/null
+++ b/dd-smoke-tests/springboot-velocity/application/gradle/wrapper/gradle-wrapper.properties
@@ -0,0 +1,8 @@
+distributionBase=GRADLE_USER_HOME
+distributionPath=wrapper/dists
+distributionSha256Sum=6f74b601422d6d6fc4e1f9a1ab6522f642c2fdcbc15ae33ebd30ba3d7198e854
+distributionUrl=https\://services.gradle.org/distributions/gradle-8.14.5-bin.zip
+networkTimeout=10000
+validateDistributionUrl=true
+zipStoreBase=GRADLE_USER_HOME
+zipStorePath=wrapper/dists
diff --git a/dd-smoke-tests/springboot-velocity/application/gradlew b/dd-smoke-tests/springboot-velocity/application/gradlew
new file mode 100755
index 00000000000..965aff38453
--- /dev/null
+++ b/dd-smoke-tests/springboot-velocity/application/gradlew
@@ -0,0 +1,183 @@
+#!/usr/bin/env sh
+
+#
+# Copyright 2015 the original author or authors.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#      https://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+#
+
+##############################################################################
+##
+##  Gradle start up script for UN*X
+##
+##############################################################################
+
+# Attempt to set APP_HOME
+# Resolve links: $0 may be a link
+PRG="$0"
+# Need this for relative symlinks.
+while [ -h "$PRG" ] ; do
+    ls=`ls -ld "$PRG"`
+    link=`expr "$ls" : '.*-> \(.*\)$'`
+    if expr "$link" : '/.*' > /dev/null; then
+        PRG="$link"
+    else
+        PRG=`dirname "$PRG"`"/$link"
+    fi
+done
+SAVED="`pwd`"
+cd "`dirname \"$PRG\"`/" >/dev/null
+APP_HOME="`pwd -P`"
+cd "$SAVED" >/dev/null
+
+APP_NAME="Gradle"
+APP_BASE_NAME=`basename "$0"`
+
+# Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+DEFAULT_JVM_OPTS='"-Xmx64m" "-Xms64m"'
+
+# Use the maximum available, or set MAX_FD != -1 to use that value.
+MAX_FD="maximum"
+
+warn () {
+    echo "$*"
+}
+
+die () {
+    echo
+    echo "$*"
+    echo
+    exit 1
+}
+
+# OS specific support (must be 'true' or 'false').
+cygwin=false
+msys=false
+darwin=false
+nonstop=false
+case "`uname`" in
+  CYGWIN* )
+    cygwin=true
+    ;;
+  Darwin* )
+    darwin=true
+    ;;
+  MINGW* )
+    msys=true
+    ;;
+  NONSTOP* )
+    nonstop=true
+    ;;
+esac
+
+CLASSPATH=$APP_HOME/gradle/wrapper/gradle-wrapper.jar
+
+
+# Determine the Java command to use to start the JVM.
+if [ -n "$JAVA_HOME" ] ; then
+    if [ -x "$JAVA_HOME/jre/sh/java" ] ; then
+        # IBM's JDK on AIX uses strange locations for the executables
+        JAVACMD="$JAVA_HOME/jre/sh/java"
+    else
+        JAVACMD="$JAVA_HOME/bin/java"
+    fi
+    if [ ! -x "$JAVACMD" ] ; then
+        die "ERROR: JAVA_HOME is set to an invalid directory: $JAVA_HOME
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+    fi
+else
+    JAVACMD="java"
+    which java >/dev/null 2>&1 || die "ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+Please set the JAVA_HOME variable in your environment to match the
+location of your Java installation."
+fi
+
+# Increase the maximum file descriptors if we can.
+if [ "$cygwin" = "false" -a "$darwin" = "false" -a "$nonstop" = "false" ] ; then
+    MAX_FD_LIMIT=`ulimit -H -n`
+    if [ $? -eq 0 ] ; then
+        if [ "$MAX_FD" = "maximum" -o "$MAX_FD" = "max" ] ; then
+            MAX_FD="$MAX_FD_LIMIT"
+        fi
+        ulimit -n $MAX_FD
+        if [ $? -ne 0 ] ; then
+            warn "Could not set maximum file descriptor limit: $MAX_FD"
+        fi
+    else
+        warn "Could not query maximum file descriptor limit: $MAX_FD_LIMIT"
+    fi
+fi
+
+# For Darwin, add options to specify how the application appears in the dock
+if $darwin; then
+    GRADLE_OPTS="$GRADLE_OPTS \"-Xdock:name=$APP_NAME\" \"-Xdock:icon=$APP_HOME/media/gradle.icns\""
+fi
+
+# For Cygwin or MSYS, switch paths to Windows format before running java
+if [ "$cygwin" = "true" -o "$msys" = "true" ] ; then
+    APP_HOME=`cygpath --path --mixed "$APP_HOME"`
+    CLASSPATH=`cygpath --path --mixed "$CLASSPATH"`
+
+    JAVACMD=`cygpath --unix "$JAVACMD"`
+
+    # We build the pattern for arguments to be converted via cygpath
+    ROOTDIRSRAW=`find -L / -maxdepth 1 -mindepth 1 -type d 2>/dev/null`
+    SEP=""
+    for dir in $ROOTDIRSRAW ; do
+        ROOTDIRS="$ROOTDIRS$SEP$dir"
+        SEP="|"
+    done
+    OURCYGPATTERN="(^($ROOTDIRS))"
+    # Add a user-defined pattern to the cygpath arguments
+    if [ "$GRADLE_CYGPATTERN" != "" ] ; then
+        OURCYGPATTERN="$OURCYGPATTERN|($GRADLE_CYGPATTERN)"
+    fi
+    # Now convert the arguments - kludge to limit ourselves to /bin/sh
+    i=0
+    for arg in "$@" ; do
+        CHECK=`echo "$arg"|egrep -c "$OURCYGPATTERN" -`
+        CHECK2=`echo "$arg"|egrep -c "^-"`                                 ### Determine if an option
+
+        if [ $CHECK -ne 0 ] && [ $CHECK2 -eq 0 ] ; then                    ### Added a condition
+            eval `echo args$i`=`cygpath --path --ignore --mixed "$arg"`
+        else
+            eval `echo args$i`="\"$arg\""
+        fi
+        i=`expr $i + 1`
+    done
+    case $i in
+        0) set -- ;;
+        1) set -- "$args0" ;;
+        2) set -- "$args0" "$args1" ;;
+        3) set -- "$args0" "$args1" "$args2" ;;
+        4) set -- "$args0" "$args1" "$args2" "$args3" ;;
+        5) set -- "$args0" "$args1" "$args2" "$args3" "$args4" ;;
+        6) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" ;;
+        7) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" ;;
+        8) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" ;;
+        9) set -- "$args0" "$args1" "$args2" "$args3" "$args4" "$args5" "$args6" "$args7" "$args8" ;;
+    esac
+fi
+
+# Escape application args
+save () {
+    for i do printf %s\\n "$i" | sed "s/'/'\\\\''/g;1s/^/'/;\$s/\$/' \\\\/" ; done
+    echo " "
+}
+APP_ARGS=`save "$@"`
+
+# Collect all arguments for the java command, following the shell quoting and substitution rules
+eval set -- $DEFAULT_JVM_OPTS $JAVA_OPTS $GRADLE_OPTS "\"-Dorg.gradle.appname=$APP_BASE_NAME\"" -classpath "\"$CLASSPATH\"" org.gradle.wrapper.GradleWrapperMain "$APP_ARGS"
+
+exec "$JAVACMD" "$@"
diff --git a/dd-smoke-tests/springboot-velocity/application/gradlew.bat b/dd-smoke-tests/springboot-velocity/application/gradlew.bat
new file mode 100644
index 00000000000..107acd32c4e
--- /dev/null
+++ b/dd-smoke-tests/springboot-velocity/application/gradlew.bat
@@ -0,0 +1,89 @@
+@rem
+@rem Copyright 2015 the original author or authors.
+@rem
+@rem Licensed under the Apache License, Version 2.0 (the "License");
+@rem you may not use this file except in compliance with the License.
+@rem You may obtain a copy of the License at
+@rem
+@rem      https://www.apache.org/licenses/LICENSE-2.0
+@rem
+@rem Unless required by applicable law or agreed to in writing, software
+@rem distributed under the License is distributed on an "AS IS" BASIS,
+@rem WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+@rem See the License for the specific language governing permissions and
+@rem limitations under the License.
+@rem
+
+@if "%DEBUG%" == "" @echo off
+@rem ##########################################################################
+@rem
+@rem  Gradle startup script for Windows
+@rem
+@rem ##########################################################################
+
+@rem Set local scope for the variables with windows NT shell
+if "%OS%"=="Windows_NT" setlocal
+
+set DIRNAME=%~dp0
+if "%DIRNAME%" == "" set DIRNAME=.
+set APP_BASE_NAME=%~n0
+set APP_HOME=%DIRNAME%
+
+@rem Resolve any "." and ".." in APP_HOME to make it shorter.
+for %%i in ("%APP_HOME%") do set APP_HOME=%%~fi
+
+@rem Add default JVM options here. You can also use JAVA_OPTS and GRADLE_OPTS to pass JVM options to this script.
+set DEFAULT_JVM_OPTS="-Xmx64m" "-Xms64m"
+
+@rem Find java.exe
+if defined JAVA_HOME goto findJavaFromJavaHome
+
+set JAVA_EXE=java.exe
+%JAVA_EXE% -version >NUL 2>&1
+if "%ERRORLEVEL%" == "0" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is not set and no 'java' command could be found in your PATH.
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:findJavaFromJavaHome
+set JAVA_HOME=%JAVA_HOME:"=%
+set JAVA_EXE=%JAVA_HOME%/bin/java.exe
+
+if exist "%JAVA_EXE%" goto execute
+
+echo.
+echo ERROR: JAVA_HOME is set to an invalid directory: %JAVA_HOME%
+echo.
+echo Please set the JAVA_HOME variable in your environment to match the
+echo location of your Java installation.
+
+goto fail
+
+:execute
+@rem Setup the command line
+
+set CLASSPATH=%APP_HOME%\gradle\wrapper\gradle-wrapper.jar
+
+
+@rem Execute Gradle
+"%JAVA_EXE%" %DEFAULT_JVM_OPTS% %JAVA_OPTS% %GRADLE_OPTS% "-Dorg.gradle.appname=%APP_BASE_NAME%" -classpath "%CLASSPATH%" org.gradle.wrapper.GradleWrapperMain %*
+
+:end
+@rem End local scope for the variables with windows NT shell
+if "%ERRORLEVEL%"=="0" goto mainEnd
+
+:fail
+rem Set variable GRADLE_EXIT_CONSOLE if you need the _script_ return code instead of
+rem the _cmd.exe /c_ return code!
+if  not "" == "%GRADLE_EXIT_CONSOLE%" exit 1
+exit /b 1
+
+:mainEnd
+if "%OS%"=="Windows_NT" endlocal
+
+:omega
diff --git a/dd-smoke-tests/springboot-velocity/application/settings.gradle b/dd-smoke-tests/springboot-velocity/application/settings.gradle
new file mode 100644
index 00000000000..25cc17e8703
--- /dev/null
+++ b/dd-smoke-tests/springboot-velocity/application/settings.gradle
@@ -0,0 +1,32 @@
+pluginManagement {
+  repositories {
+    mavenLocal()
+    if (settings.hasProperty("gradlePluginProxy")) {
+      maven {
+        url settings["gradlePluginProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    if (settings.hasProperty("mavenRepositoryProxy")) {
+      maven {
+        url settings["mavenRepositoryProxy"]
+        allowInsecureProtocol = true
+      }
+    }
+    gradlePluginPortal()
+    mavenCentral()
+  }
+}
+
+def isCI = providers.environmentVariable("CI").isPresent()
+
+if (isCI) {
+  def sharedRootDir = "$rootDir/../../../"
+  buildCache {
+    local {
+      directory = "$sharedRootDir/workspace/build-cache"
+    }
+  }
+}
+
+rootProject.name='springboot-velocity-smoketest'
diff --git a/dd-smoke-tests/springboot-velocity/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java b/dd-smoke-tests/springboot-velocity/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
similarity index 100%
rename from dd-smoke-tests/springboot-velocity/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
rename to dd-smoke-tests/springboot-velocity/application/src/main/java/datadog/smoketest/springboot/SpringbootApplication.java
diff --git a/dd-smoke-tests/springboot-velocity/src/main/java/datadog/smoketest/springboot/XssController.java b/dd-smoke-tests/springboot-velocity/application/src/main/java/datadog/smoketest/springboot/XssController.java
similarity index 100%
rename from dd-smoke-tests/springboot-velocity/src/main/java/datadog/smoketest/springboot/XssController.java
rename to dd-smoke-tests/springboot-velocity/application/src/main/java/datadog/smoketest/springboot/XssController.java
diff --git a/dd-smoke-tests/springboot-velocity/src/main/resources/templates/velocity-insecure.vm b/dd-smoke-tests/springboot-velocity/application/src/main/resources/templates/velocity-insecure.vm
similarity index 100%
rename from dd-smoke-tests/springboot-velocity/src/main/resources/templates/velocity-insecure.vm
rename to dd-smoke-tests/springboot-velocity/application/src/main/resources/templates/velocity-insecure.vm
diff --git a/dd-smoke-tests/springboot-velocity/src/main/resources/templates/velocity-secure.vm b/dd-smoke-tests/springboot-velocity/application/src/main/resources/templates/velocity-secure.vm
similarity index 100%
rename from dd-smoke-tests/springboot-velocity/src/main/resources/templates/velocity-secure.vm
rename to dd-smoke-tests/springboot-velocity/application/src/main/resources/templates/velocity-secure.vm
diff --git a/dd-smoke-tests/springboot-velocity/build.gradle b/dd-smoke-tests/springboot-velocity/build.gradle
index 76881a53bc1..b169b5f424f 100644
--- a/dd-smoke-tests/springboot-velocity/build.gradle
+++ b/dd-smoke-tests/springboot-velocity/build.gradle
@@ -1,34 +1,70 @@
-import org.springframework.boot.gradle.tasks.bundling.BootJar
+apply from: "$rootDir/gradle/java.gradle"
 
-plugins {
-  id 'java'
-  id 'org.springframework.boot' version '2.7.15'
-  id 'io.spring.dependency-management' version '1.0.15.RELEASE'
-  id 'java-test-fixtures'
-}
+apply plugin: 'java-test-fixtures'
 
-apply from: "$rootDir/gradle/java.gradle"
-apply from: "$rootDir/gradle/spring-boot-plugin.gradle"
 description = 'SpringBoot Velocity Smoke Tests.'
 
-dependencies {
-  implementation group: 'org.springframework.boot', name: 'spring-boot-starter-web', version: '1.5.18.RELEASE'
-  implementation group: 'org.apache.velocity', name: 'velocity', version: '1.5'
-  implementation(group: 'org.apache.velocity', name: 'velocity-tools', version: '1.3') {
-    exclude group: 'javax.servlet', module: 'servlet-api'
-  }
+def appDir = "$projectDir/application"
+def appBuildDir = "$buildDir/application"
+def isWindows = System.getProperty("os.name").toLowerCase().contains("win")
+def gradlewCommand = isWindows ? 'gradlew.bat' : 'gradlew'
+
+tasks.register('bootJar', Exec) {
+  workingDir appDir
+  environment += [
+    "GRADLE_OPTS": "-Dorg.gradle.jvmargs='-Xmx512M'",
+    "JAVA_HOME": getLazyJavaHomeFor(8)
+  ]
+  commandLine "$appDir/${gradlewCommand}", "bootJar", "--no-daemon", "--max-workers=4", "-PappBuildDir=$appBuildDir"
+
+  outputs.cacheIf { true }
+
+  outputs.dir(appBuildDir)
+    .withPropertyName("applicationJar")
+
+  inputs.files(fileTree(appDir) {
+    include '**/*'
+    exclude '.gradle/**'
+  })
+  .withPropertyName("application")
+  .withPathSensitivity(PathSensitivity.RELATIVE)
+}
 
+dependencies {
   testImplementation project(':dd-smoke-tests')
   testImplementation(testFixtures(project(":dd-smoke-tests:iast-util")))
 }
 
+// The XssController loads templates from the filesystem at "resources/main/templates"
+// relative to the test's working directory (= this module's buildDir). Mirror the app's
+// processed resources here so the path resolves correctly at runtime.
+tasks.register('copyAppResources', Copy) {
+  dependsOn 'bootJar'
+  from "$appBuildDir/resources/main"
+  into "$buildDir/resources/main"
+}
+
+// jar reads build/resources/main; declare the dependency so Gradle knows the ordering.
+tasks.named('jar') {
+  dependsOn 'copyAppResources'
+}
+
 tasks.withType(Test).configureEach {
-  dependsOn "bootJar"
-  def bootJarTask = tasks.named('bootJar', BootJar)
+  dependsOn 'copyAppResources'
   jvmArgumentProviders.add(new CommandLineArgumentProvider() {
       @Override
       Iterable<String> asArguments() {
-        return bootJarTask.map { ["-Ddatadog.smoketest.springboot.shadowJar.path=${it.archiveFile.get()}"] }.get()
+        return ["-Ddatadog.smoketest.springboot.shadowJar.path=$appBuildDir/libs/springboot-velocity-smoketest.jar"]
       }
     })
 }
+
+spotless {
+  java {
+    target "**/*.java"
+  }
+
+  groovyGradle {
+    target '*.gradle', "**/*.gradle"
+  }
+}