diff --git a/packages/aws-cdk/lib/api/deploy-stack.ts b/packages/aws-cdk/lib/api/deploy-stack.ts
index 626dcce5c57e7..86d1dc4828e1d 100644
--- a/packages/aws-cdk/lib/api/deploy-stack.ts
+++ b/packages/aws-cdk/lib/api/deploy-stack.ts
@@ -440,6 +440,12 @@ async function canSkipDeploy(
     return false;
   }
 
+  // Existing stack is in a failed state
+  if (cloudFormationStack.stackStatus.isFailure) {
+    debug(`${deployName}: stack is in a failure state`);
+    return false;
+  }
+
   // We can skip deploy
   return true;
 }
diff --git a/packages/aws-cdk/test/api/deploy-stack.test.ts b/packages/aws-cdk/test/api/deploy-stack.test.ts
index 6e45a20acc770..9f061a2214d13 100644
--- a/packages/aws-cdk/test/api/deploy-stack.test.ts
+++ b/packages/aws-cdk/test/api/deploy-stack.test.ts
@@ -423,6 +423,27 @@ test('deploy not skipped if template did not change but one tag removed', async
   expect(cfnMocks.getTemplate).toHaveBeenCalledWith({ StackName: 'withouterrors', TemplateStage: 'Original' });
 });
 
+test('deploy is not skipped if stack is in a _FAILED state', async () => {
+  // GIVEN
+  givenTemplateIs(FAKE_STACK.template);
+  givenStackExists({
+    StackStatus: 'DELETE_FAILED',
+  });
+
+  // WHEN
+  let err;
+  await deployStack({
+    stack: FAKE_STACK,
+    sdk,
+    sdkProvider,
+    resolvedEnvironment: mockResolvedEnvironment(),
+    usePreviousParameters: true,
+  }).catch(e => err = e);
+
+  // THEN
+  expect(err).toEqual(Error('The stack named withouterrors failed to deploy: DELETE_FAILED'));
+});
+
 test('existing stack in UPDATE_ROLLBACK_COMPLETE state can be updated', async () => {
   // GIVEN
   givenStackExists(