diff --git a/dd-smoke-tests/gradle/src/test/groovy/datadog/smoketest/AbstractGradleTest.groovy b/dd-smoke-tests/gradle/src/test/groovy/datadog/smoketest/AbstractGradleTest.groovy
index 3dc0b365c9a..991df1a9658 100644
--- a/dd-smoke-tests/gradle/src/test/groovy/datadog/smoketest/AbstractGradleTest.groovy
+++ b/dd-smoke-tests/gradle/src/test/groovy/datadog/smoketest/AbstractGradleTest.groovy
@@ -34,6 +34,8 @@ class AbstractGradleTest extends CiVisibilitySmokeTest {
   private static final String GRADLE_TEST_RESOURCE_EXTENSION = ".gradleTest"
   private static final String GRADLE_REGULAR_EXTENSION = ".gradle"
 
+  private static final ComparableVersion GRADLE_9 = new ComparableVersion("9.0.0")
+
   @TempDir
   protected Path projectFolder
 
@@ -105,23 +107,23 @@ class AbstractGradleTest extends CiVisibilitySmokeTest {
     } else if (Jvm.current.java17) {
       return gradleVersion.compareTo(new ComparableVersion("7.3")) >= 0
     } else if (Jvm.current.java16) {
-      return gradleVersion.compareTo(new ComparableVersion("7.0")) >= 0
+      return gradleVersion.isWithin(new ComparableVersion("7.0"), GRADLE_9)
     } else if (Jvm.current.java15) {
-      return gradleVersion.compareTo(new ComparableVersion("6.7")) >= 0
+      return gradleVersion.isWithin(new ComparableVersion("6.7"), GRADLE_9)
     } else if (Jvm.current.java14) {
-      return gradleVersion.compareTo(new ComparableVersion("6.3")) >= 0
+      return gradleVersion.isWithin(new ComparableVersion("6.3"), GRADLE_9)
     } else if (Jvm.current.java13) {
-      return gradleVersion.compareTo(new ComparableVersion("6.0")) >= 0
+      return gradleVersion.isWithin(new ComparableVersion("6.0"), GRADLE_9)
     } else if (Jvm.current.java12) {
-      return gradleVersion.compareTo(new ComparableVersion("5.4")) >= 0
+      return gradleVersion.isWithin(new ComparableVersion("5.4"), GRADLE_9)
     } else if (Jvm.current.java11) {
-      return gradleVersion.compareTo(new ComparableVersion("5.0")) >= 0
+      return gradleVersion.isWithin(new ComparableVersion("5.0"), GRADLE_9)
     } else if (Jvm.current.java10) {
-      return gradleVersion.compareTo(new ComparableVersion("4.7")) >= 0
+      return gradleVersion.isWithin(new ComparableVersion("4.7"), GRADLE_9)
     } else if (Jvm.current.java9) {
-      return gradleVersion.compareTo(new ComparableVersion("4.3")) >= 0
+      return gradleVersion.isWithin(new ComparableVersion("4.3"), GRADLE_9)
     } else if (Jvm.current.java8) {
-      return gradleVersion.compareTo(new ComparableVersion("2.0")) >= 0
+      return gradleVersion.isWithin(new ComparableVersion("2.0"), GRADLE_9)
     }
     return false
   }
diff --git a/dd-smoke-tests/gradle/src/test/groovy/datadog/smoketest/GradleLauncherSmokeTest.groovy b/dd-smoke-tests/gradle/src/test/groovy/datadog/smoketest/GradleLauncherSmokeTest.groovy
index 13f017d4ae3..f0ed1de85c8 100644
--- a/dd-smoke-tests/gradle/src/test/groovy/datadog/smoketest/GradleLauncherSmokeTest.groovy
+++ b/dd-smoke-tests/gradle/src/test/groovy/datadog/smoketest/GradleLauncherSmokeTest.groovy
@@ -2,6 +2,7 @@ package datadog.smoketest
 
 import datadog.communication.util.IOUtils
 import datadog.trace.civisibility.utils.ShellCommandExecutor
+import spock.util.environment.Jvm
 
 /**
  * This test runs Gradle Launcher with the Java Tracer injected
@@ -12,6 +13,7 @@ class GradleLauncherSmokeTest extends AbstractGradleTest {
   private static final int GRADLE_BUILD_TIMEOUT_MILLIS = 90_000
 
   private static final String AGENT_JAR = System.getProperty("datadog.smoketest.agent.shadowJar.path")
+  private static final String JAVA_HOME = buildJavaHome()
 
   def "test Gradle Launcher injects tracer into Gradle Daemon: v#gradleVersion, cmd line - #gradleDaemonCmdLineParams"() {
     given:
@@ -45,18 +47,19 @@ class GradleLauncherSmokeTest extends AbstractGradleTest {
   }
 
   private void givenGradleWrapper(String gradleVersion) {
-    def shellCommandExecutor = new ShellCommandExecutor(projectFolder.toFile(), GRADLE_BUILD_TIMEOUT_MILLIS)
+    def shellCommandExecutor = new ShellCommandExecutor(projectFolder.toFile(), GRADLE_BUILD_TIMEOUT_MILLIS, ["JAVA_HOME": JAVA_HOME])
     shellCommandExecutor.executeCommand(IOUtils::readFully, "./gradlew", "wrapper", "--gradle-version", gradleVersion)
   }
 
   private String whenRunningGradleLauncherWithJavaTracerInjected(String gradleDaemonCmdLineParams) {
     def shellCommandExecutor = new ShellCommandExecutor(projectFolder.toFile(), GRADLE_BUILD_TIMEOUT_MILLIS, [
-      "GRADLE_OPTS"                        : "-javaagent:${AGENT_JAR}".toString(),
-      "DD_CIVISIBILITY_ENABLED"            : "true",
-      "DD_CIVISIBILITY_AGENTLESS_ENABLED"  : "true",
-      "DD_CIVISIBILITY_AGENTLESS_URL"      : "${mockBackend.intakeUrl}".toString(),
-      "DD_CIVISIBILITY_GIT_UPLOAD_ENABLED" : "false",
-      "DD_API_KEY"                         : "dummy"
+      "JAVA_HOME"                         : JAVA_HOME,
+      "GRADLE_OPTS"                       : "-javaagent:${AGENT_JAR}".toString(),
+      "DD_CIVISIBILITY_ENABLED"           : "true",
+      "DD_CIVISIBILITY_AGENTLESS_ENABLED" : "true",
+      "DD_CIVISIBILITY_AGENTLESS_URL"     : "${mockBackend.intakeUrl}".toString(),
+      "DD_CIVISIBILITY_GIT_UPLOAD_ENABLED": "false",
+      "DD_API_KEY"                        : "dummy"
     ])
     String[] command = ["./gradlew", "--no-daemon", "--info"]
     if (gradleDaemonCmdLineParams) {
@@ -74,4 +77,12 @@ class GradleLauncherSmokeTest extends AbstractGradleTest {
     }
     return true
   }
+
+  private static String buildJavaHome() {
+    if (Jvm.current.isJava8()) {
+      return System.getenv("JAVA_8_HOME")
+    } else {
+      return System.getenv("JAVA_" + Jvm.current.getJavaSpecificationVersion() + "_HOME")
+    }
+  }
 }
diff --git a/dd-smoke-tests/gradle/src/test/resources/test-succeed-gradle-plugin-test/build.gradleTest b/dd-smoke-tests/gradle/src/test/resources/test-succeed-gradle-plugin-test/build.gradleTest
index 4e71ba3bc73..b2d6847a8ed 100644
--- a/dd-smoke-tests/gradle/src/test/resources/test-succeed-gradle-plugin-test/build.gradleTest
+++ b/dd-smoke-tests/gradle/src/test/resources/test-succeed-gradle-plugin-test/build.gradleTest
@@ -30,6 +30,7 @@ repositories {
 dependencies {
     testImplementation gradleTestKit()
 
+    testImplementation 'org.junit.platform:junit-platform-launcher'
     testImplementation 'org.junit.jupiter:junit-jupiter-engine:5.10.2'
 }
 
diff --git a/dd-smoke-tests/gradle/src/test/resources/test-succeed-junit-5/build.gradleTest b/dd-smoke-tests/gradle/src/test/resources/test-succeed-junit-5/build.gradleTest
index b1c3cff6d5c..30687787ef7 100644
--- a/dd-smoke-tests/gradle/src/test/resources/test-succeed-junit-5/build.gradleTest
+++ b/dd-smoke-tests/gradle/src/test/resources/test-succeed-junit-5/build.gradleTest
@@ -19,7 +19,7 @@ repositories {
 testing {
     suites {
         test {
-            useJUnitJupiter()
+            useJUnitJupiter('5.9.3')
 
             dependencies {
               implementation 'org.junit.platform:junit-platform-launcher:1.9.3'
diff --git a/internal-api/src/main/java/datadog/trace/util/ComparableVersion.java b/internal-api/src/main/java/datadog/trace/util/ComparableVersion.java
index 147607c71f0..7411667e39f 100644
--- a/internal-api/src/main/java/datadog/trace/util/ComparableVersion.java
+++ b/internal-api/src/main/java/datadog/trace/util/ComparableVersion.java
@@ -9,6 +9,7 @@
 import java.util.List;
 import java.util.Locale;
 import java.util.Properties;
+import javax.annotation.Nonnull;
 
 // backported from org.apache.maven:maven-artifact:3.9.9
 public class ComparableVersion implements Comparable<ComparableVersion> {
@@ -125,6 +126,11 @@ public int compareTo(ComparableVersion o) {
     return this.items.compareTo(o.items);
   }
 
+  /** Checks if the version is in the range {@code [start, end)} */
+  public boolean isWithin(@Nonnull ComparableVersion start, @Nonnull ComparableVersion end) {
+    return compareTo(start) >= 0 && compareTo(end) < 0;
+  }
+
   public String toString() {
     return this.value;
   }