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diff --git a/‎dd-java-agent/agent-tooling/src/main/java/datadog/trace/agent/tooling/context/MapBackedProvider.java‎
Lines changed: 2 additions & 45 deletions b/‎dd-java-agent/agent-tooling/src/main/java/datadog/trace/agent/tooling/context/MapBackedProvider.java‎
Lines changed: 2 additions & 45 deletions
diff --git a/‎dd-java-agent/agent-tooling/src/test/groovy/datadog/trace/agent/test/context/MapBackedProviderTest.groovy‎
Lines changed: 0 additions & 162 deletions b/‎dd-java-agent/agent-tooling/src/test/groovy/datadog/trace/agent/test/context/MapBackedProviderTest.groovy‎
Lines changed: 0 additions & 162 deletions
diff --git a/‎dd-java-agent/agent-tooling/src/test/java/datadog/trace/agent/test/context/BadClassToRemap.java‎
Lines changed: 0 additions & 20 deletions b/‎dd-java-agent/agent-tooling/src/test/java/datadog/trace/agent/test/context/BadClassToRemap.java‎
Lines changed: 0 additions & 20 deletions
diff --git a/‎dd-java-agent/agent-tooling/src/test/java/datadog/trace/agent/test/context/ClassToRemap.java‎
Lines changed: 0 additions & 32 deletions b/‎dd-java-agent/agent-tooling/src/test/java/datadog/trace/agent/test/context/ClassToRemap.java‎
Lines changed: 0 additions & 32 deletions
diff --git a/‎dd-java-agent/testing/src/test/groovy/context/MapBackedProviderTest.groovy‎
Lines changed: 54 additions & 0 deletions b/‎dd-java-agent/testing/src/test/groovy/context/MapBackedProviderTest.groovy‎
Lines changed: 54 additions & 0 deletions
@@ -10,7 +10,6 @@
 import java.lang.reflect.Method;
 import java.util.HashMap;
 import java.util.Map;
-import java.util.Set;
 import java.util.UUID;
 import java.util.concurrent.atomic.AtomicReference;
 import jdk.internal.org.objectweb.asm.ClassWriter;
@@ -112,7 +111,8 @@ public DynamicType.Builder<?> transform(
                   return injector.transform(
                       builder,
                       typeDescription,
-                      findClassLoaderForMapHolderInjection(classLoader),
+                      // dynamic map classes will always go to the bootstrap
+                      BOOTSTRAP_CLASSLOADER,
                       module);
                 }
               });
@@ -259,49 +259,6 @@ public void visitLdcInsn(Object value) {
     };
   }
 
-  /**
-   * Find the topmost classloader in the classloader hierarchy (beginning from startingLoader) which
-   * can load all user classes defined in the instrumentation context store.
-   */
-  private ClassLoader findClassLoaderForMapHolderInjection(final ClassLoader startingLoader) {
-    final Set<String> userClassNames = instrumenter.contextStore().keySet();
-    ClassLoader lastGoodLoader = startingLoader;
-    ClassLoader searchLoader = startingLoader;
-    // search up the classloader hierarchy for a classloader which can see all user classes
-    while (true) {
-      log.debug(
-          "{}: Searching for classloader to inject dynamic context map: {}",
-          instrumenter,
-          searchLoader);
-      if (searchLoader == BOOTSTRAP_CLASSLOADER) {
-        searchLoader = Utils.getBootstrapProxy();
-      }
-      boolean allClassesFound = true;
-      for (final String userClassName : userClassNames) {
-        if (searchLoader.getResource(Utils.getResourceName(userClassName)) == null) {
-          allClassesFound = false;
-          break;
-        }
-      }
-      if (!allClassesFound) {
-        // current searchLoader can't see resources. Use last good classloader.
-        break;
-      }
-      lastGoodLoader = searchLoader;
-      if (searchLoader == Utils.getBootstrapProxy()) {
-        // all classloaders can see resources. Use bootstrap
-        searchLoader = BOOTSTRAP_CLASSLOADER;
-        lastGoodLoader = BOOTSTRAP_CLASSLOADER;
-        break;
-      }
-      searchLoader = searchLoader.getParent();
-    }
-
-    log.debug(
-        "{}: Found classloader to inject dynamic context map: {}", instrumenter, lastGoodLoader);
-    return lastGoodLoader;
-  }
-
   private Map<String, byte[]> dynamicClasses() {
     return createOrGetDynamicClasses();
   }
 
@@ -0,0 +1,54 @@
+package context
+
+import datadog.trace.agent.test.AgentTestRunner
+import datadog.trace.agent.test.TestUtils
+import net.bytebuddy.utility.JavaModule
+
+import java.lang.ref.WeakReference
+
+class MapBackedProviderTest extends AgentTestRunner {
+
+  def setupSpec() {
+    assert new UserClass1().isInstrumented()
+  }
+
+  @Override
+  boolean onInstrumentationError(
+    final String typeName,
+    final ClassLoader classLoader,
+    final JavaModule module,
+    final boolean loaded,
+    final Throwable throwable) {
+    // UserClass2 asserts on incorrect api usage. Error expected.
+    return !(typeName.equals(UserClass2.getName()) && throwable.getMessage().startsWith("Incorrect Context Api Usage detected."))
+  }
+
+  def "correct api usage stores state in map"() {
+    when:
+    UserClass1 instance1 = new UserClass1()
+    UserClass1 instance2 = new UserClass1()
+    instance1.incrementContextCount()
+
+    then:
+    instance1.incrementContextCount() == 2
+    instance2.incrementContextCount() == 1
+  }
+
+  def "backing map should not create strong refs to user instances"() {
+    when:
+    UserClass1 instance = new UserClass1()
+    final int count = instance.incrementContextCount()
+    WeakReference<UserClass1> instanceRef = new WeakReference(instance)
+    instance = null
+    TestUtils.awaitGC(instanceRef)
+
+    then:
+    instanceRef.get() == null
+    count == 1
+  }
+
+  def "incorrect api usage fails at class load time"() {
+    expect:
+    !new UserClass2().isInstrumented()
+  }
+}