diff --git a/lib/internal/debugger/inspect.js b/lib/internal/debugger/inspect.js
index 42b5c64ab87029..e006f513f9b93f 100644
--- a/lib/internal/debugger/inspect.js
+++ b/lib/internal/debugger/inspect.js
@@ -45,7 +45,7 @@ const debuglog = util.debuglog('inspect');
 
 const { ERR_DEBUGGER_STARTUP_ERROR } = require('internal/errors').codes;
 
-async function portIsFree(host, port, timeout = 9999) {
+async function portIsFree(host, port, timeout = 3000) {
   if (port === 0) return; // Binding to a random port.
 
   const retryDelay = 150;
@@ -64,7 +64,10 @@ async function portIsFree(host, port, timeout = 9999) {
     const error = await new Promise((resolve) => {
       const socket = net.connect(port, host);
       socket.on('error', resolve);
-      socket.on('connect', resolve);
+      socket.on('connect', () => {
+        socket.end();
+        resolve();
+      });
     });
     if (error?.code === 'ECONNREFUSED') {
       return;
diff --git a/test/common/debugger.js b/test/common/debugger.js
index d2ac4f3b6c5fbf..4aff5b9a0f74d9 100644
--- a/test/common/debugger.js
+++ b/test/common/debugger.js
@@ -7,7 +7,13 @@ const BREAK_MESSAGE = new RegExp('(?:' + [
   'exception', 'other', 'promiseRejection',
 ].join('|') + ') in', 'i');
 
-const TIMEOUT = common.platformTimeout(5000);
+let TIMEOUT = common.platformTimeout(5000);
+if (common.isWindows) {
+  // Some of the windows machines in the CI need more time to receive
+  // the outputs from the client.
+  // https://github.com/nodejs/build/issues/3014
+  TIMEOUT = common.platformTimeout(15000);
+}
 
 function isPreBreak(output) {
   return /Break on start/.test(output) && /1 \(function \(exports/.test(output);