diff --git a/news/3 Code Health/6322.md b/news/3 Code Health/6322.md
new file mode 100644
index 000000000000..33f7837b8547
--- /dev/null
+++ b/news/3 Code Health/6322.md	
@@ -0,0 +1 @@
+Retry failing debugger test (retry due to intermittent issues on `Azure Pipelines`).
diff --git a/src/test/debugger/attach.ptvsd.test.ts b/src/test/debugger/attach.ptvsd.test.ts
index fd88a04ee42f..5ace57371215 100644
--- a/src/test/debugger/attach.ptvsd.test.ts
+++ b/src/test/debugger/attach.ptvsd.test.ts
@@ -139,5 +139,7 @@ suite('Debugging - Attach Debugger', () => {
     }
     test('Confirm we are able to attach to a running program', async () => {
         await testAttachingToRemoteProcess(path.dirname(fileToDebug), path.dirname(fileToDebug), IS_WINDOWS);
-    });
+    })
+        // Retry as tests can timeout on server due to connectivity issues.
+        .retries(3);
 });