This is one of the most common Outlook complaints. You type your password, click OK, and a few seconds later the box appears again. It can loop indefinitely. Here is how to break the cycle.

Step 1: Make Sure the Password Is Actually Correct

Before anything else, sign in to your email provider's website directly (outlook.com, mail.google.com, etc.) to confirm your password works. If you cannot log in on the website, reset your password there first, then come back to fix Outlook.

Step 2: Clear Stored Credentials in Windows

Windows saves email credentials in the Credential Manager, and stale entries cause the loop.

  1. Open Control Panel > Credential Manager.
  2. Click Windows Credentials.
  3. Look for entries that mention your email address, MicrosoftOffice, or MAPI.
  4. Click each one and choose Remove.
  5. Restart Outlook and enter your password when prompted. This time, tick Remember my credentials.

Step 3: Check the Remember Password Option in Outlook

Go to File > Account Settings > Account Settings, select your account, and click Change. Make sure Remember password is checked. If it is greyed out, your organisation may have a policy preventing it — contact your IT team.

Step 4: Remove and Re-Add the Account

In File > Account Settings, remove the account, then add it again from scratch. This creates a fresh authentication token and usually solves the problem when the above steps do not.

Step 5: For Microsoft 365 / Work Accounts

Work accounts using Modern Authentication sometimes get into a token loop. Sign out of Outlook completely: go to File > Office Account > Sign Out, close Outlook, reopen it, and sign in again. Also check that your Windows account is connected to your work Microsoft 365 account under Settings > Accounts > Access work or school.

If the prompts persist after all of this, ask us — it may be a policy or multi-factor authentication issue that needs a closer look.