diff --git a/extension/src/client.ts b/extension/src/client.ts
index bbec5ea64..9df39ea2f 100644
--- a/extension/src/client.ts
+++ b/extension/src/client.ts
@@ -30,9 +30,7 @@ import { LoggerStream } from './LoggerSteam';
 const localize = nls.loadMessageBundle();
 
 export class GradleTasksClient implements vscode.Disposable {
-  // The connectDeadline is a high number because, even though the Java process has been
-  // started, the gGRPC server is not yet ready to accept connections.
-  private connectDeadline = 120;
+  private connectDeadline = 5; // seconds
   private grpcClient: GrpcClient | null = null;
   private _onConnect: vscode.EventEmitter<null> = new vscode.EventEmitter<
     null
diff --git a/extension/src/server.ts b/extension/src/server.ts
index 322521797..04ff0c1eb 100644
--- a/extension/src/server.ts
+++ b/extension/src/server.ts
@@ -4,7 +4,7 @@ import * as nls from 'vscode-nls';
 
 import { logger } from './logger';
 import { buildGradleServerTask } from './tasks';
-import { isDebuggingServer } from './util';
+import { isDebuggingServer, waitOnTcp } from './util';
 
 const localize = nls.loadMessageBundle();
 
@@ -38,11 +38,18 @@ export class GradleTasksServer implements vscode.Disposable {
     private readonly context: vscode.ExtensionContext
   ) {
     context.subscriptions.push(
-      vscode.tasks.onDidStartTaskProcess((event) => {
+      vscode.tasks.onDidStartTaskProcess(async (event) => {
         if (event.execution.task.name === SERVER_TASK_NAME) {
           if (isProcessRunning(event.processId)) {
-            logger.debug('Gradle server process started');
-            this.fireOnReady();
+            logger.debug(
+              'Gradle server process started, waiting for server to start'
+            );
+            try {
+              await waitOnTcp('localhost', this.port!);
+              this.fireOnReady();
+            } catch (e) {
+              logger.error('Gradle server not started:', e.message);
+            }
           } else {
             logger.error('Gradle server processes not started');
           }
diff --git a/extension/src/test/testUtil.ts b/extension/src/test/testUtil.ts
index dd48e5f56..aee14181c 100644
--- a/extension/src/test/testUtil.ts
+++ b/extension/src/test/testUtil.ts
@@ -23,7 +23,7 @@ export function createTestRunner(pattern: string) {
     // Create the mocha test
     const mocha = new Mocha({
       ui: 'bdd',
-      timeout: 130000,
+      timeout: 60000,
       color: true,
     });
     mocha.bail(true);
diff --git a/extension/src/util.ts b/extension/src/util.ts
index d32d406a7..c1543ea9a 100644
--- a/extension/src/util.ts
+++ b/extension/src/util.ts
@@ -6,6 +6,7 @@ export const isTest = (): boolean =>
 export const isDebuggingServer = (): boolean =>
   process.env.VSCODE_DEBUG_SERVER?.toLowerCase() === 'true';
 
+const maximumTimeout = 120000; // 2 minutes
 const tcpTimeout = 300;
 
 function tcpExists(host: string, port: number): Promise<boolean> {
@@ -27,14 +28,21 @@ function tcpExists(host: string, port: number): Promise<boolean> {
   });
 }
 
-async function tryConnect(host: string, port: number): Promise<void> {
+async function tryConnect(
+  host: string,
+  port: number,
+  startTime: number
+): Promise<void> {
   const connected = await tcpExists(host, port);
   if (connected) {
     return;
   }
-  await tryConnect(host, port);
+  if (Date.now() - startTime >= maximumTimeout) {
+    throw new Error('Unable to wait on tcp due to maxmium timeout reached');
+  }
+  await tryConnect(host, port, startTime);
 }
 
 export function waitOnTcp(host: string, port: number): Promise<void> {
-  return tryConnect(host, port);
+  return tryConnect(host, port, Date.now());
 }