diff --git a/packages/core-api/src/lib/loginPopup.test.ts b/packages/core-api/src/lib/loginPopup.test.ts
index 55f1408e8d..6527618ef7 100644
--- a/packages/core-api/src/lib/loginPopup.test.ts
+++ b/packages/core-api/src/lib/loginPopup.test.ts
@@ -156,6 +156,15 @@ describe('showLoginPopup', () => {
     expect(addEventListenerSpy).toBeCalledTimes(1);
     expect(removeEventListenerSpy).toBeCalledTimes(0);
 
+    const listener = addEventListenerSpy.mock.calls[0][1] as EventListener;
+    listener({
+      source: popupMock,
+      origin: 'origin',
+      data: {
+        targetOrigin: 'http://localhost',
+      },
+    } as MessageEvent);
+
     setTimeout(() => {
       popupMock.closed = true;
     }, 150);
@@ -167,4 +176,41 @@ describe('showLoginPopup', () => {
     expect(addEventListenerSpy).toBeCalledTimes(1);
     expect(removeEventListenerSpy).toBeCalledTimes(1);
   });
+
+  it('should indicate if origin does not match', async () => {
+    const openSpy = jest
+      .spyOn(window, 'open')
+      .mockReturnValue({ closed: false } as Window);
+    const addEventListenerSpy = jest.spyOn(window, 'addEventListener');
+    const removeEventListenerSpy = jest.spyOn(window, 'removeEventListener');
+    const popupMock = { closed: false };
+
+    openSpy.mockReturnValue(popupMock as Window);
+
+    const payloadPromise = showLoginPopup({
+      url: 'url',
+      name: 'name',
+      origin: 'origin',
+    });
+
+    const listener = addEventListenerSpy.mock.calls[0][1] as EventListener;
+    listener({
+      source: popupMock,
+      origin: 'origin',
+      data: {
+        targetOrigin: 'http://differenthost',
+      },
+    } as MessageEvent);
+
+    setTimeout(() => {
+      popupMock.closed = true;
+    }, 150);
+    await expect(payloadPromise).rejects.toThrow(
+      'Login failed, incorrect app origin',
+    );
+
+    expect(openSpy).toBeCalledTimes(1);
+    expect(addEventListenerSpy).toBeCalledTimes(1);
+    expect(removeEventListenerSpy).toBeCalledTimes(1);
+  });
 });
diff --git a/packages/core-api/src/lib/loginPopup.ts b/packages/core-api/src/lib/loginPopup.ts
index 10d6efd7a4..5c6d424363 100644
--- a/packages/core-api/src/lib/loginPopup.ts
+++ b/packages/core-api/src/lib/loginPopup.ts
@@ -79,6 +79,8 @@ export function showLoginPopup(options: LoginPopupOptions): Promise<any> {
       `menubar=no,location=no,resizable=no,scrollbars=no,status=no,width=${width},height=${height},top=${top},left=${left}`,
     );
 
+    let targetOrigin = '';
+
     if (!popup || typeof popup.closed === 'undefined' || popup.closed) {
       reject(new Error('Failed to open auth popup.'));
       return;
@@ -92,6 +94,12 @@ export function showLoginPopup(options: LoginPopupOptions): Promise<any> {
         return;
       }
       const { data } = event;
+
+      if (data.targetOrigin) {
+        targetOrigin = data.targetOrigin;
+        return;
+      }
+
       if (data.type !== 'authorization_response') {
         return;
       }
@@ -111,7 +119,12 @@ export function showLoginPopup(options: LoginPopupOptions): Promise<any> {
 
     const intervalId = setInterval(() => {
       if (popup.closed) {
-        const error = new Error('Login failed, popup was closed');
+        const errMessage = `Login failed, ${
+          targetOrigin !== window.location.origin
+            ? 'incorrect app origin'
+            : 'popup was closed'
+        }`;
+        const error = new Error(errMessage);
         error.name = 'PopupClosedError';
         reject(error);
         done();
diff --git a/plugins/auth-backend/src/lib/flow/authFlowHelpers.test.ts b/plugins/auth-backend/src/lib/flow/authFlowHelpers.test.ts
index 6c49eaf351..5e4e5f875b 100644
--- a/plugins/auth-backend/src/lib/flow/authFlowHelpers.test.ts
+++ b/plugins/auth-backend/src/lib/flow/authFlowHelpers.test.ts
@@ -81,6 +81,52 @@ describe('oauth helpers', () => {
       expect(mockResponse.end).toBeCalledWith(expect.stringContaining(encoded));
     });
 
+    it('should call postMessage twice but only one of them with target *', () => {
+      let responseBody: String;
+
+      const mockResponse = ({
+        end: jest.fn(function (body) {
+          responseBody = body;
+          return this;
+        }),
+        setHeader: jest.fn().mockReturnThis(),
+      } as unknown) as express.Response;
+
+      const data: WebMessageResponse = {
+        type: 'authorization_response',
+        response: {
+          providerInfo: {
+            accessToken: 'ACCESS_TOKEN',
+            idToken: 'ID_TOKEN',
+            expiresInSeconds: 10,
+            scope: 'email',
+          },
+          profile: {
+            email: 'foo@bar.com',
+          },
+          backstageIdentity: {
+            id: 'a',
+            idToken: 'a.b.c',
+          },
+        },
+      };
+      postMessageResponse(mockResponse, appOrigin, data);
+      expect(responseBody.match(/.postMessage\(/g)).toHaveLength(2);
+      expect(
+        responseBody.match(/.postMessage\([a-zA-z.()]*, \'\*\'\)/g),
+      ).toHaveLength(1);
+
+      const errData: WebMessageResponse = {
+        type: 'authorization_response',
+        error: new Error('Unknown error occurred'),
+      };
+      postMessageResponse(mockResponse, appOrigin, errData);
+      expect(responseBody.match(/.postMessage\(/g)).toHaveLength(2);
+      expect(
+        responseBody.match(/.postMessage\([a-zA-z.()]*, \'\*\'\)/g),
+      ).toHaveLength(1);
+    });
+
     it('handles single quotes and unicode chars safely', () => {
       const mockResponse = ({
         end: jest.fn().mockReturnThis(),
diff --git a/plugins/auth-backend/src/lib/flow/authFlowHelpers.ts b/plugins/auth-backend/src/lib/flow/authFlowHelpers.ts
index d2a9557a28..5aba427905 100644
--- a/plugins/auth-backend/src/lib/flow/authFlowHelpers.ts
+++ b/plugins/auth-backend/src/lib/flow/authFlowHelpers.ts
@@ -38,10 +38,24 @@ export const postMessageResponse = (
   // data.
 
   // TODO: Make target app origin configurable globally
+
+  //
+  // postMessage fails silently if the targetOrigin is disallowed.
+  // So 2 postMessages are sent from the popup to the parent window.
+  // First, the origin being used to post the actual authorization response is
+  // shared with the parent window with a postMessage with targetOrigin '*'.
+  // Second, the actual authorization response is sent with the app origin
+  // as the targetOrigin.
+  // If the first message was received but the actual auth response was
+  // never received, the event listener can conclude that targetOrigin
+  // was disallowed, indicating potential misconfiguration.
+  //
   const script = `
-    var json = decodeURIComponent('${base64Data}');
+    var authResponse = decodeURIComponent('${base64Data}');
     var origin = decodeURIComponent('${base64Origin}');
-    (window.opener || window.parent).postMessage(JSON.parse(json), origin);
+    var originInfo = {'targetOrigin': origin};
+    (window.opener || window.parent).postMessage(originInfo, '*');
+    (window.opener || window.parent).postMessage(JSON.parse(authResponse), origin);
     window.close();
   `;
   const hash = crypto.createHash('sha256').update(script).digest('base64');