Yahoo Email Sign In Prompt Repeatedly Pops Up In Outlook 365 Email ...

Question

Yahoo keeps asking for my password to access Microsoft Outlook 365 despite checking to box to stay logged in.

Answer 1

This typically happens when Yahoo does not like the authentication method Outlook is using. Try generating an app password in your Yahoo account and use that in Microsoft Outlook, it usually stops the repeated login prompts

Answer 2

Yahoo sign-in prompts in Outlook 365 usually indicate an authentication or password mismatch between Yahoo and the credentials stored in Outlook.

Try these steps in order:

1. Confirm the Yahoo password
   • Sign in directly at the Yahoo website to verify the current password works.
   • If sign-in fails, reset the password using Yahoo’s process, then try Outlook again.
2. If the password was changed, update it in Outlook
   • When the Yahoo prompt appears in Outlook after a password change, enter the new password so Outlook can store and reuse it.
   • Outlook will keep asking until the stored password matches what Yahoo expects.
3. Check for common sign-in issues
   • Ensure Caps Lock is off; passwords are case-sensitive.
   • Verify the full Yahoo email address is used as the username.
4. If prompts continue after confirming the password
   • Remove the Yahoo account from Outlook and add it again so Outlook can re-establish a clean connection and token with Yahoo.
   • During re-add, complete all Yahoo consent/authorization screens so Outlook is fully authorized to access the account.
5. If the issue persists only in classic Outlook
   • Consider using the new Outlook for Windows, which can handle modern authentication flows more reliably for some third-party providers.

If the problem started after changing the Yahoo password or if the password has expired, it is necessary to update the password stored in Outlook after changing it on Yahoo’s site.

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References:

• Troubleshoot Outlook email setup
• Change or update your email password in Outlook for Windows
• Yahoo Account No Longer Syncing to Outlook - Microsoft Q&A
• Do you know how to fix the issue where Outlook keeps prompting for a password even though credentials are saved - Microsoft Q&A
• Outlook ask for credentials every minute - Microsoft Q&A