diff --git a/dd-smoke-tests/maven/src/test/groovy/datadog/smoketest/MavenSmokeTest.groovy b/dd-smoke-tests/maven/src/test/groovy/datadog/smoketest/MavenSmokeTest.groovy
index d213f3a0784..ff039e7e51e 100644
--- a/dd-smoke-tests/maven/src/test/groovy/datadog/smoketest/MavenSmokeTest.groovy
+++ b/dd-smoke-tests/maven/src/test/groovy/datadog/smoketest/MavenSmokeTest.groovy
@@ -333,7 +333,7 @@ class MavenSmokeTest extends CiVisibilitySmokeTest {
 
     if (!p.waitFor(PROCESS_TIMEOUT_SECS, TimeUnit.SECONDS)) {
       p.destroyForcibly()
-      throw new TimeoutException("Instrumented process failed to exit")
+      throw new TimeoutException("Instrumented process failed to exit within $PROCESS_TIMEOUT_SECS")
     }
 
     return p.exitValue()
diff --git a/gradle/configure_tests.gradle b/gradle/configure_tests.gradle
index 945a9e9665b..849827fa06f 100644
--- a/gradle/configure_tests.gradle
+++ b/gradle/configure_tests.gradle
@@ -124,3 +124,13 @@ if (!project.property("activePartition")) {
     }
   }
 }
+
+tasks.withType(Test) {
+  // https://docs.gradle.com/develocity/flaky-test-detection/
+  // https://docs.gradle.com/develocity/gradle-plugin/current/#test_retry
+  develocity.testRetry {
+    if (System.getenv().containsKey("CI")) {
+      maxRetries = 3
+    }
+  }
+}