Ever since day one at Adobe I’ve had an odd issue with Outlook on my Mac. About 3-4 times a day it would ‘forget’ my password. As soon as I entered my password it worked, but it bugged me that I had to keep re-entering it. I Googled but never found the right answer.
I deleted and recreated my profile numerous times, but it never helped. Finally, (fellow Adobe evangelist!) made a simple suggest.
Instead of entering my password in Outlook, I should be doing it in the Exchange settings via System Preferences. So first you go here And then click Details: That was it. I can’t believe I didn’t figure that out earlier, but every single time I tried to fix it by Googling around I never came across this solution.
(Probably because it was too obvious.;).
This will fix your issue Like Outlook Keeps Asking for username and Password, Outlook Keeps asking for the password in Popup Window. This method works with every version of Outlook. THE FIX: think of Mac Mail as an app for a phone & set up two step authentication.let windows/outlook.live generate a password for you “app” (Mac Mail) Copy THAT password and use it for hotmail in Mac Mail NOT the one you use when you sign into windows.live or outlook or hotmail.
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