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Office 365 keeps prompting for login credentials within Mac OSX? I came across a problem where a client of mine had bought and installed Office Suite 2016 she than upgraded to Office 365 Business Premium.

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  • Glad you got it resolved, keychain issues can be a real pain. I'd just recommend adding more details to your next question, this was a bit vague IMHO.
    – SamAndrew81
    Commented Feb 1, 2017 at 16:42

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Here is what solved it for me. (Copied from: https://answers.microsoft.com/en-us/msoffice/forum/msoffice_outlook-mso_mac/authentication-failedcheck-your-account/063826c1-1e4c-40ba-9bfa-54e745925fc1 )

  1. Quit all Office applications (Word, Teams, Outlook, etc)
  2. Go to KeyChain Access.
  3. Search "Exchange" under Login --> All Items and delete everything.
  4. Search "Office" and delete everything.
  5. Search "ADAL" and delete everything.
  6. Launch Outlook.
  7. You will get the activation prompt and then If account is already added you will see the password prompt for app and ADAL again. Please do 2-Factor Authentication if asked to.
  8. If that doesn't work, do steps 2-4 but restart the Mac before launching Outlook.
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    The restart did it for me. Many of the other topics out on the net don't mention restarting the entire macbook - but that was necessary for me. Without restarting, I kept running into the same issue.
    – KFox112
    Commented Feb 19, 2020 at 22:21
  • Thank you, ADAL search retrieves old items from a time machine restoration that others posts didn't mentions
    – Oscar
    Commented May 7 at 10:09
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I had to uninstall office suite and clear keychain for Microsoft Office, once that was established Office 365 no longer kept prompting for key and user credentials. Hope this helps!

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My issue was that, every time upon starting Outlook, I was prompted to "Sign in with your organizational account". I fixed it by going to Preferences > Accounts, removing my account, and adding it again.

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I had mitmproxy installed (but not running?). Uninstalling it allowed the login process to work correctly.

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Removing (deleting) the exchange account in Outlook, letting it fully delete, then adding it again as recommended by ognockocaten worked for me!

This problem showed up after changing the user's login name on O365.

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    That's great, and we're happy for you. But on any Stack Exchange site, instead of posting a "me too" answer, you should instead upvote the answer which worked for you -- in this case, the answer by @ognockocaten. To do that, click the upwards pointing arrow to the left of the answer. When you earn more reputation on the site you'll be able to post comments on answers, such as this one I'm writing to you.
    – Brett Donald
    Commented Oct 15, 2019 at 0:36

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