diff --git a/instrumentation/vertx/vertx-web-3.0/javaagent/build.gradle.kts b/instrumentation/vertx/vertx-web-3.0/javaagent/build.gradle.kts
index ee63a8871aeb..ea68aebda4f9 100644
--- a/instrumentation/vertx/vertx-web-3.0/javaagent/build.gradle.kts
+++ b/instrumentation/vertx/vertx-web-3.0/javaagent/build.gradle.kts
@@ -20,45 +20,59 @@ dependencies {
   testInstrumentation(project(":instrumentation:jdbc:javaagent"))
 }
 
+val testLatestDeps = findProperty("testLatestDeps") as Boolean
+
 testing {
   suites {
     val version3Test by registering(JvmTestSuite::class) {
       dependencies {
         implementation(project(":instrumentation:vertx:vertx-web-3.0:testing"))
 
-        implementation("io.vertx:vertx-web:3.0.0")
-        implementation("io.vertx:vertx-jdbc-client:3.0.0")
-        implementation("io.vertx:vertx-codegen:3.0.0")
-        implementation("io.vertx:vertx-docgen:3.0.0")
+        val version = if (testLatestDeps) "3.+" else "3.0.0"
+        implementation("io.vertx:vertx-web:$version")
+        implementation("io.vertx:vertx-jdbc-client:$version")
+        implementation("io.vertx:vertx-codegen:$version")
+        implementation("io.vertx:vertx-docgen:$version")
       }
     }
 
-    val latestDepTest by registering(JvmTestSuite::class) {
+    val version41Test by registering(JvmTestSuite::class) {
       dependencies {
         implementation(project(":instrumentation:vertx:vertx-web-3.0:testing"))
 
-        implementation("io.vertx:vertx-web:4.+")
-        implementation("io.vertx:vertx-jdbc-client:4.+")
-        implementation("io.vertx:vertx-codegen:4.+")
+        val version = if (testLatestDeps) "4.+" else "4.1.0"
+        implementation("io.vertx:vertx-web:$version")
+        implementation("io.vertx:vertx-jdbc-client:$version")
+        implementation("io.vertx:vertx-codegen:$version")
+      }
+    }
+
+    val version5Test by registering(JvmTestSuite::class) {
+      dependencies {
+        implementation(project(":instrumentation:vertx:vertx-web-3.0:testing"))
+
+        val version = if (testLatestDeps) "latest.release" else "5.0.0"
+        implementation("io.vertx:vertx-web:$version")
+        implementation("io.vertx:vertx-jdbc-client:$version")
+        implementation("io.vertx:vertx-codegen:$version")
       }
     }
   }
 }
 
-val testLatestDeps = findProperty("testLatestDeps") as Boolean
-
 tasks {
-  if (testLatestDeps) {
-    // disable regular test running and compiling tasks when latest dep test task is run
-    named("test") {
+  named("compileVersion5TestJava", JavaCompile::class).configure {
+    options.release.set(11)
+  }
+  val testJavaVersion =
+    gradle.startParameter.projectProperties.get("testJavaVersion")?.let(JavaVersion::toVersion)
+      ?: JavaVersion.current()
+  if (!testJavaVersion.isCompatibleWith(JavaVersion.VERSION_11)) {
+    named("version5Test", Test::class).configure {
       enabled = false
     }
   }
 
-  named("latestDepTest") {
-    enabled = testLatestDeps
-  }
-
   check {
     dependsOn(testing.suites)
   }
diff --git a/instrumentation/vertx/vertx-web-3.0/javaagent/src/latestDepTest/java/io/netty/handler/codec/haproxy/HAProxyMessage.java b/instrumentation/vertx/vertx-web-3.0/javaagent/src/version41Test/java/io/netty/handler/codec/haproxy/HAProxyMessage.java
similarity index 100%
rename from instrumentation/vertx/vertx-web-3.0/javaagent/src/latestDepTest/java/io/netty/handler/codec/haproxy/HAProxyMessage.java
rename to instrumentation/vertx/vertx-web-3.0/javaagent/src/version41Test/java/io/netty/handler/codec/haproxy/HAProxyMessage.java
diff --git a/instrumentation/vertx/vertx-web-3.0/javaagent/src/latestDepTest/java/io/netty/handler/codec/haproxy/HAProxyProxiedProtocol.java b/instrumentation/vertx/vertx-web-3.0/javaagent/src/version41Test/java/io/netty/handler/codec/haproxy/HAProxyProxiedProtocol.java
similarity index 100%
rename from instrumentation/vertx/vertx-web-3.0/javaagent/src/latestDepTest/java/io/netty/handler/codec/haproxy/HAProxyProxiedProtocol.java
rename to instrumentation/vertx/vertx-web-3.0/javaagent/src/version41Test/java/io/netty/handler/codec/haproxy/HAProxyProxiedProtocol.java
diff --git a/instrumentation/vertx/vertx-web-3.0/javaagent/src/latestDepTest/java/io/opentelemetry/javaagent/instrumentation/vertx/VertxLatestHttpServerTest.java b/instrumentation/vertx/vertx-web-3.0/javaagent/src/version41Test/java/io/opentelemetry/javaagent/instrumentation/vertx/Vertx41HttpServerTest.java
similarity index 78%
rename from instrumentation/vertx/vertx-web-3.0/javaagent/src/latestDepTest/java/io/opentelemetry/javaagent/instrumentation/vertx/VertxLatestHttpServerTest.java
rename to instrumentation/vertx/vertx-web-3.0/javaagent/src/version41Test/java/io/opentelemetry/javaagent/instrumentation/vertx/Vertx41HttpServerTest.java
index f13cff89107c..17276048611c 100644
--- a/instrumentation/vertx/vertx-web-3.0/javaagent/src/latestDepTest/java/io/opentelemetry/javaagent/instrumentation/vertx/VertxLatestHttpServerTest.java
+++ b/instrumentation/vertx/vertx-web-3.0/javaagent/src/version41Test/java/io/opentelemetry/javaagent/instrumentation/vertx/Vertx41HttpServerTest.java
@@ -8,11 +8,11 @@
 import io.vertx.core.AbstractVerticle;
 import io.vertx.core.Vertx;
 
-class VertxLatestHttpServerTest extends AbstractVertxHttpServerTest {
+class Vertx41HttpServerTest extends AbstractVertxHttpServerTest {
 
   @Override
   protected Class<? extends AbstractVerticle> verticle() {
-    return VertxLatestWebServer.class;
+    return Vertx41WebServer.class;
   }
 
   @Override
diff --git a/instrumentation/vertx/vertx-web-3.0/javaagent/src/latestDepTest/java/io/opentelemetry/javaagent/instrumentation/vertx/VertxLatestWebServer.java b/instrumentation/vertx/vertx-web-3.0/javaagent/src/version41Test/java/io/opentelemetry/javaagent/instrumentation/vertx/Vertx41WebServer.java
similarity index 92%
rename from instrumentation/vertx/vertx-web-3.0/javaagent/src/latestDepTest/java/io/opentelemetry/javaagent/instrumentation/vertx/VertxLatestWebServer.java
rename to instrumentation/vertx/vertx-web-3.0/javaagent/src/version41Test/java/io/opentelemetry/javaagent/instrumentation/vertx/Vertx41WebServer.java
index fa268df6cea7..b467d076e91e 100644
--- a/instrumentation/vertx/vertx-web-3.0/javaagent/src/latestDepTest/java/io/opentelemetry/javaagent/instrumentation/vertx/VertxLatestWebServer.java
+++ b/instrumentation/vertx/vertx-web-3.0/javaagent/src/version41Test/java/io/opentelemetry/javaagent/instrumentation/vertx/Vertx41WebServer.java
@@ -9,7 +9,7 @@
 import io.vertx.core.http.HttpServerResponse;
 import io.vertx.ext.web.Router;
 
-public class VertxLatestWebServer extends AbstractVertxWebServer {
+public class Vertx41WebServer extends AbstractVertxWebServer {
 
   @Override
   public void end(HttpServerResponse response) {
diff --git a/instrumentation/vertx/vertx-web-3.0/javaagent/src/version5Test/java/io/netty/handler/codec/haproxy/HAProxyMessage.java b/instrumentation/vertx/vertx-web-3.0/javaagent/src/version5Test/java/io/netty/handler/codec/haproxy/HAProxyMessage.java
new file mode 100644
index 000000000000..3dcf2cafedfe
--- /dev/null
+++ b/instrumentation/vertx/vertx-web-3.0/javaagent/src/version5Test/java/io/netty/handler/codec/haproxy/HAProxyMessage.java
@@ -0,0 +1,10 @@
+/*
+ * Copyright The OpenTelemetry Authors
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+package io.netty.handler.codec.haproxy;
+
+// instrumentation fails without this class
+@SuppressWarnings("checkstyle:AbbreviationAsWordInName")
+public class HAProxyMessage {}
diff --git a/instrumentation/vertx/vertx-web-3.0/javaagent/src/version5Test/java/io/netty/handler/codec/haproxy/HAProxyProxiedProtocol.java b/instrumentation/vertx/vertx-web-3.0/javaagent/src/version5Test/java/io/netty/handler/codec/haproxy/HAProxyProxiedProtocol.java
new file mode 100644
index 000000000000..5659024f96a0
--- /dev/null
+++ b/instrumentation/vertx/vertx-web-3.0/javaagent/src/version5Test/java/io/netty/handler/codec/haproxy/HAProxyProxiedProtocol.java
@@ -0,0 +1,10 @@
+/*
+ * Copyright The OpenTelemetry Authors
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+package io.netty.handler.codec.haproxy;
+
+// instrumentation fails without this class
+@SuppressWarnings("checkstyle:AbbreviationAsWordInName")
+public class HAProxyProxiedProtocol {}
diff --git a/instrumentation/vertx/vertx-web-3.0/javaagent/src/version5Test/java/io/opentelemetry/javaagent/instrumentation/vertx/Vertx5HttpServerTest.java b/instrumentation/vertx/vertx-web-3.0/javaagent/src/version5Test/java/io/opentelemetry/javaagent/instrumentation/vertx/Vertx5HttpServerTest.java
new file mode 100644
index 000000000000..bd5dae62d57c
--- /dev/null
+++ b/instrumentation/vertx/vertx-web-3.0/javaagent/src/version5Test/java/io/opentelemetry/javaagent/instrumentation/vertx/Vertx5HttpServerTest.java
@@ -0,0 +1,60 @@
+/*
+ * Copyright The OpenTelemetry Authors
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+package io.opentelemetry.javaagent.instrumentation.vertx;
+
+import io.vertx.core.AbstractVerticle;
+import io.vertx.core.DeploymentOptions;
+import io.vertx.core.Vertx;
+import io.vertx.core.VertxOptions;
+import io.vertx.core.json.JsonObject;
+import java.util.concurrent.CompletableFuture;
+import java.util.concurrent.ExecutionException;
+import java.util.concurrent.TimeUnit;
+import java.util.concurrent.TimeoutException;
+
+class Vertx5HttpServerTest extends AbstractVertxHttpServerTest {
+
+  @Override
+  protected Class<? extends AbstractVerticle> verticle() {
+    return Vertx5WebServer.class;
+  }
+
+  @Override
+  protected Vertx setupServer()
+      throws ExecutionException, InterruptedException, TimeoutException, NoSuchMethodException {
+    Vertx server =
+        Vertx.vertx(
+            new VertxOptions()
+            // Useful for debugging:
+            // .setBlockedThreadCheckInterval(Integer.MAX_VALUE)
+            );
+    CompletableFuture<Void> future = new CompletableFuture<>();
+
+    server
+        .deployVerticle(
+            verticle().getName(),
+            new DeploymentOptions()
+                .setConfig(
+                    new JsonObject()
+                        .put(AbstractVertxWebServer.CONFIG_HTTP_SERVER_PORT, (Object) port))
+                .setInstances(3))
+        .onComplete(
+            res -> {
+              if (!res.succeeded()) {
+                throw new IllegalStateException("Cannot deploy server Verticle", res.cause());
+              }
+              future.complete(null);
+            });
+
+    future.get(30, TimeUnit.SECONDS);
+    return server;
+  }
+
+  @Override
+  protected void stopServer(Vertx server) throws Exception {
+    server.close();
+  }
+}
diff --git a/instrumentation/vertx/vertx-web-3.0/javaagent/src/version5Test/java/io/opentelemetry/javaagent/instrumentation/vertx/Vertx5WebServer.java b/instrumentation/vertx/vertx-web-3.0/javaagent/src/version5Test/java/io/opentelemetry/javaagent/instrumentation/vertx/Vertx5WebServer.java
new file mode 100644
index 000000000000..9eb314040fd4
--- /dev/null
+++ b/instrumentation/vertx/vertx-web-3.0/javaagent/src/version5Test/java/io/opentelemetry/javaagent/instrumentation/vertx/Vertx5WebServer.java
@@ -0,0 +1,37 @@
+/*
+ * Copyright The OpenTelemetry Authors
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+package io.opentelemetry.javaagent.instrumentation.vertx;
+
+import io.vertx.core.Promise;
+import io.vertx.core.http.HttpServerResponse;
+import io.vertx.ext.web.Router;
+
+public class Vertx5WebServer extends AbstractVertxWebServer {
+
+  @Override
+  public void end(HttpServerResponse response) {
+    response.end();
+  }
+
+  @Override
+  public void end(HttpServerResponse response, String message) {
+    response.end(message);
+  }
+
+  @Override
+  public void start(Promise<Void> startPromise) {
+    int port = config().getInteger(CONFIG_HTTP_SERVER_PORT);
+    Router router = buildRouter();
+    Router mainRouter = Router.router(vertx);
+    mainRouter.route("/vertx-app/*").subRouter(router);
+
+    vertx
+        .createHttpServer()
+        .requestHandler(mainRouter)
+        .listen(port)
+        .onComplete(it -> startPromise.complete());
+  }
+}