(New) Outlook keeps asking me to sign in every second

No. It didn't.

I can sign into the email and account just fine via my browser but not when using Outlook. It worked fine for years until this week. And I have 7 emails with Google Workspace and only one doesn't work.

James Mc

Dear James Mc,

Thank you for posting your question to the Microsoft Q&A. I understand how annoying it is to be stuck in a sign-in loop, especially when the instructions you find online don't match what you see on your screen.

The reason those instructions aren't matching up is likely because they refer to the "Classic" version of Outlook, while you are likely using a newer version or a different view. That discrepancy in the "File" menu is a very common point of confusion.

Since the menus aren't matching, you can actually bypass Outlook completely and fix this directly in Windows settings. Here are the steps to clear that "stuck" password from your system's memory.

Step 1: Clear the "Stuck" Password (Credential Manager)

Your computer sometimes holds onto an old or corrupted password file, which causes the loop. 

1. Close Outlook completely.
2. Click the Start Menu (Windows logo) and type: Credential Manager.
3. Click the icon that appears (it looks like a safe/keys).
4. Click the box that says Windows Credentials.
5. Scroll down the list (it is alphabetical). Look for anything that starts with:
   • MicrosoftOffice16_Data:SSPI...
   • Outlook...
   • Or the specific email address that is having the problem.
6. Click the arrow to expand the entry and select Remove.
   • Note: Do this for every entry that references that specific email address or "Office16".
7. Crucial Step: Restart your computer. This flushes the memory and ensures the old data is truly gone.
8. Open Outlook. It should ask you for the password one last time. Enter it, check "Remember my credentials," and see if it sticks.

Step 2: The "Control Panel" Method (If Step 1 fails)

If the loop persists, we can force a fresh connection using the old Control Panel interface.

1. Close Outlook.
2. Press the Windows Key + R on your keyboard.
3. Type control and press Enter.
4. In the top right "Search Control Panel" box, type: Mail.
5. Click on Mail (Microsoft Outlook).
6. Click the Email Accounts... button.
7. You will see a simple list of your email accounts. Select the one that is looping.
8. Click Remove. (Don't worry, your emails are safe on the server).
9. Once it is gone, click New...
10. Type your Name, Email, and Password.

Why this works: This forces Outlook to open a "Modern" sign-in window (usually a web pop-up). This modern window creates a new, secure connection that usually bypasses the loop entirely.

I hope this helps you finally break that cycle! Please let me know if you have other questions