diff --git a/src/main/java/com/spotify/github/v3/checks/Annotation.java b/src/main/java/com/spotify/github/v3/checks/Annotation.java
index 6f8465fe..4f055af3 100644
--- a/src/main/java/com/spotify/github/v3/checks/Annotation.java
+++ b/src/main/java/com/spotify/github/v3/checks/Annotation.java
@@ -22,6 +22,7 @@
 
 import com.fasterxml.jackson.annotation.JsonInclude;
 import com.fasterxml.jackson.databind.annotation.JsonDeserialize;
+import com.google.common.base.Preconditions;
 import com.spotify.github.GithubStyle;
 import java.util.Optional;
 import org.immutables.value.Value;
@@ -114,4 +115,23 @@ public interface Annotation {
    * @return the optional
    */
   Optional<Integer> endColumn();
+
+  /**
+   * Automatically validates the maximum length of properties.
+   *
+   * GitHub does not validate these properly on their side (at least in GHE 3.2)
+   * and returns 5xx HTTP responses instead. To avoid that, let's validate the data
+   * in this client library.
+   */
+  @Value.Check
+  @SuppressWarnings("checkstyle:magicnumber")
+  default void check() {
+    // max values from https://docs.github.com/en/rest/checks/runs
+    Preconditions.checkState(title().map(String::length).orElse(0) <= 255,
+        "'title' exceeded max length of 255");
+    Preconditions.checkState(message().length() <= 64 * 1024,
+        "'message' exceeded max length of 64kB");
+    Preconditions.checkState(rawDetails().map(String::length).orElse(0) <= 64 * 1024,
+        "'rawDetails' exceeded max length of 64kB");
+  }
 }
diff --git a/src/main/java/com/spotify/github/v3/checks/CheckRunAction.java b/src/main/java/com/spotify/github/v3/checks/CheckRunAction.java
index feb81b3e..f3c93c9b 100644
--- a/src/main/java/com/spotify/github/v3/checks/CheckRunAction.java
+++ b/src/main/java/com/spotify/github/v3/checks/CheckRunAction.java
@@ -21,6 +21,7 @@
 package com.spotify.github.v3.checks;
 
 import com.fasterxml.jackson.databind.annotation.JsonDeserialize;
+import com.google.common.base.Preconditions;
 import com.spotify.github.GithubStyle;
 import org.immutables.value.Value;
 
@@ -57,4 +58,23 @@ public interface CheckRunAction {
    * @return the string
    */
   String description();
+
+  /**
+   * Automatically validates the maximum length of properties.
+   *
+   * GitHub does not validate these properly on their side (at least in GHE 3.2)
+   * and returns 5xx HTTP responses instead. To avoid that, let's validate the data
+   * in this client library.
+   */
+  @Value.Check
+  @SuppressWarnings("checkstyle:magicnumber")
+  default void check() {
+    // max values from https://docs.github.com/en/rest/checks/runs
+    Preconditions.checkState(label().length() <= 20,
+        "'label' exceeded max length of 20");
+    Preconditions.checkState(identifier().length() <= 20,
+        "'identifier' exceeded max length of 20");
+    Preconditions.checkState(description().length() <= 40,
+        "'description' exceeded max length of 40");
+  }
 }
diff --git a/src/test/java/com/spotify/github/v3/checks/AnnotationTest.java b/src/test/java/com/spotify/github/v3/checks/AnnotationTest.java
new file mode 100644
index 00000000..7c48d6b8
--- /dev/null
+++ b/src/test/java/com/spotify/github/v3/checks/AnnotationTest.java
@@ -0,0 +1,69 @@
+/*-
+ * -\-\-
+ * github-client
+ * --
+ * Copyright (C) 2016 - 2022 Spotify AB
+ * --
+ * 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
+ *
+ *      http://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.
+ * -/-/-
+ */
+
+package com.spotify.github.v3.checks;
+
+import static org.hamcrest.CoreMatchers.is;
+import static org.hamcrest.MatcherAssert.assertThat;
+import static org.junit.jupiter.api.Assertions.assertThrows;
+
+import com.spotify.github.FixtureHelper;
+import com.spotify.github.jackson.Json;
+import com.spotify.github.v3.checks.ImmutableAnnotation.Builder;
+import java.io.IOException;
+import java.time.ZonedDateTime;
+import org.junit.Test;
+
+public class AnnotationTest {
+   private Builder builder() {
+     return ImmutableAnnotation.builder()
+         .title("title")
+         .message("message")
+         .rawDetails("rawDetails")
+         .path("path")
+         .startLine(1)
+         .endLine(2)
+         .annotationLevel(AnnotationLevel.notice);
+   }
+
+  @Test
+  public void allowsCreationWithinLimits(){
+    builder().build();
+
+    builder()
+        .title("a".repeat(255))
+        .message("a".repeat(64000))
+        .rawDetails("a".repeat(64000))
+        .build();
+  }
+
+  @Test
+  public void failsCreationWhenMaxLengthExceeded(){
+    assertThrows(IllegalStateException.class, () ->
+    builder().title("a".repeat(256)).build()
+    );
+    assertThrows(IllegalStateException.class, () ->
+        builder().message("a".repeat(66000)).build()
+    );
+    assertThrows(IllegalStateException.class, () ->
+        builder().rawDetails("a".repeat(66000)).build()
+    );
+  }
+}
diff --git a/src/test/java/com/spotify/github/v3/checks/CheckRunActionTest.java b/src/test/java/com/spotify/github/v3/checks/CheckRunActionTest.java
new file mode 100644
index 00000000..0646fb7c
--- /dev/null
+++ b/src/test/java/com/spotify/github/v3/checks/CheckRunActionTest.java
@@ -0,0 +1,65 @@
+/*-
+ * -\-\-
+ * github-client
+ * --
+ * Copyright (C) 2016 - 2022 Spotify AB
+ * --
+ * 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
+ *
+ *      http://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.
+ * -/-/-
+ */
+
+package com.spotify.github.v3.checks;
+
+import static org.hamcrest.CoreMatchers.is;
+import static org.hamcrest.MatcherAssert.assertThat;
+import static org.junit.jupiter.api.Assertions.assertThrows;
+
+import com.spotify.github.FixtureHelper;
+import com.spotify.github.jackson.Json;
+import com.spotify.github.v3.checks.ImmutableCheckRunAction.Builder;
+import java.io.IOException;
+import java.time.ZonedDateTime;
+import org.junit.Test;
+
+public class CheckRunActionTest {
+  private Builder builder() {
+    return ImmutableCheckRunAction.builder()
+        .label("label")
+        .identifier("identifier")
+        .description("description");
+  }
+
+  @Test
+  public void allowsCreationWithinLimits(){
+    builder().build();
+
+    builder()
+        .label("a".repeat(20))
+        .identifier("a".repeat(20))
+        .description("a".repeat(40))
+        .build();
+  }
+
+  @Test
+  public void failsCreationWhenMaxLengthExceeded(){
+    assertThrows(IllegalStateException.class, () ->
+        builder().label("a".repeat(21)).build()
+    );
+    assertThrows(IllegalStateException.class, () ->
+        builder().identifier("a".repeat(21)).build()
+    );
+    assertThrows(IllegalStateException.class, () ->
+        builder().description("a".repeat(41)).build()
+    );
+  }
+}