Hotmail account keeps logging out of Outlook

Question

This has been happening for days now. I have an hotmail account setup in my Outlook app on my Mac that logs out daily. So, I need to sign in daily.

When I try to sign in, I am prompted to do it with a passkey or external something - I have no idea what these are and have never set this up, it just randomly started asking for it. Only when I fail to use a passkey can I try to "sign in using a different method", giving me the option of good old password or a code sent to my alternative email. When I try the password it tells me that MY PASSWORD IS WRONG (which I find baffling, since I have reset it recently and I am currently logged on with said password on the browser) and that I have tried too many times with the wrong password. I can only login with the alternative email, but the next day I have to do it all again.

What is going on and how do I disable a passkey? How do I reset this whole thing? I absolutely do not want a passkey, I just want to be able to login with my regular password. I have both password and email enabled in the security settings, and have MFA disabled.

Thank you!!

Answer 1

Please note that this is a user-to-user community. As moderators, I have limited access to internal development details. My role is to direct users to the appropriate support channels and resources. While I cannot provide backend analysis, I will do my best to assist you within my responsibilities. 

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Hi Maria

I understand you are having problem with a Hotmail account in Outlook on Mac that logs out daily, then forces passkey prompts and rejects the password even though the same password works in the browser. Please also follow these steps: 

• Remove/disable the passkey prompt by removing saved passkeys on the Microsoft account 
  • Sign in to Advanced Security Options and remove the passkey from “Ways to prove who you are”.  
  • Only remove the passkey entry you don’t want (do not remove all security info). See: Manage your saved passkeys - Microsoft Support 
  • If you still see passkey prompts during sign-in, you can choose Sign-in options / Other ways to sign in and pick a different method.  
  • If the prompt errors out or says the passkey can’t be used, delete passkeys that no longer apply and setting up/using an alternate sign-in method.  
• Force a clean re-auth across devices  
  • Use Microsoft’s “Sign out everywhere” from Advanced security options, then sign back in fresh on the Mac. 
• Re-sync the account in Outlook for Mac  
  • In Outlook for Mac: Tools > Accounts > select the Hotmail account > click the three dots at bottom left > Reset Account. This forces Outlook to re-sync the account.  
• If Outlook for Mac says the password is wrong (while web works), sync the current password into Outlook for Mac 
  • Change the password with the provider first (you already did), then update/sync it in Outlook for Mac: Tools > Accounts > select the account > use the indicator next to the account name to re-enter the username/password when prompted. 
• If sign-in is being blocked/locked or keeps failing in-app 
  • Fill in the account recovery form with as much information as possible and contact support immediately if the form fails:  
  • Visit Contact - Microsoft Support 
  • Type a brief description of your issue in the search box  
  • Scroll down to the bottom > select Sign in to contact support  
  • Log in to another available personal Microsoft account.   
  • Under Products & Services, select "Other Products"; Under Categories, select "Manage account security", and click Confirm.  
  • Click "Chat with a support agent in your web browser" (during business hours) 

Thank you for your understanding. Have a lovely day! 

Answer 2

The behavior matches a sign-in/authentication problem on Outlook for Mac with a Microsoft (Hotmail/Outlook.com) account, where cached tokens or keychain items are corrupted and Outlook keeps forcing re‑authentication.

To stabilize sign-in on the Mac side, reset Outlook’s cached credentials and keychain access so it can store a fresh, valid sign-in state:

1. Quit Outlook and all other Office apps (Word, Excel, PowerPoint, OneNote).
2. Open Keychain Access on the Mac (via Spotlight search for “Keychain Access”).
3. In the search box, look for items related to Office sign-in and tokens, and remove them so Outlook can recreate them:
   • Search for Exchange and delete items for the Hotmail/Outlook account.
   • Search for adal and delete items of type MicrosoftOffice15_2_Data:ADAL:<GUID>.
   • Search for office and delete Microsoft Office Identities Cache 2 and Microsoft Office Identities Settings 2.
4. Still in Keychain Access, select the login keychain in the top-left pane, then from the File menu choose Lock Keychain "login".
5. Start any Office app (for example, Word). When prompted for keychain access, enter the Mac admin password and allow access.
6. When prompted, sign in with the Hotmail/Microsoft account using the preferred method (password plus any required verification).
7. Quit the app and reopen it to confirm it no longer repeatedly prompts.
8. Open Outlook and add/sign in to the Hotmail account again; Outlook should now keep the session instead of logging out daily.

If Outlook for Mac is an older build (for example, Outlook 2016 for Mac), also ensure it is updated to a current version, as older builds had issues with duplicate tokens causing repeated authentication prompts.

Passkey prompts are part of modern sign-in flows. They appear when the sign-in page detects that passkeys or WebAuthn/FIDO methods are available, but they do not permanently replace password sign-in. After clearing the cached tokens and keychain entries and signing in again, Outlook should stop looping on the passkey prompt and respect the chosen method (password plus email code) without forcing daily re‑authentication.

If sign-in to the Hotmail/Outlook.com account itself is intermittently blocked or rate-limited (for example, “too many attempts”), use the Outlook.com/Hotmail sign-in troubleshooter and, if necessary, wait for any temporary lockout to clear before trying again.

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References:

• Outlook 2016 for Mac repeatedly prompts for authentication
• Office for Mac repeatedly requesting keychain access
• How to sign in to Hotmail