Outlook for windows won't connect to outlook server, keeps asking password

Copper Contributor

Hi there.


I am experiencing the following extremely frustrating problem for the last 10 days or so. I have an Office 365 Family subscription and been using an outlook personalized email (domain-at-domain.com) for about a year or so, without any problems. My mail client is Outlook for Windows both on my laptop and my work PC and I am also using the Outlook app for my android devices (Mobile and Tablet).


Things were working flawlessly for more than a year and all of a sudden, last week, Outlook (both on my PC and my laptop) started repeatedly asking for my password for using the outlook SMTP server, although I never changed my password. After hitting OK a few times, the message stopped popping up, only to appear again randomly throughout the day.


Since 3-4 days ago, the message stopped appearing for the SMTP server, but started appearing for the outlook.office365.com server (screenshot 1).





I tried everything,  cleared all passwords from Windows Credential manager, removed the email account from outlook and created it again (using IMAP, since auto configuration never worked neither now not in the past), used app password for 2FA instead of my normal Outlook/Microsoft password, nothing worked. I installed Thunderbird and setup the outlook email there, the problem still persisted (screenshot 2).





Weird thing is, after hitting OK 2-3 times, both programs (Outlook for Windows and Thunderbird) finally connect to the server and sync my emails, meaning the username and password combo is not wrong !! Also, no problem whatsoever in the Outlook app for Android on my mobile or tablet.



What in the world is happening ? Can it be a problem on the server's (outlook's) end ? And if yes, why doesn't it affect the Android apps ? I have installed Brave Browser about 10 days ago both on my PC and laptop (was using Chrome up until then). Can Brave be causing the problem through a way I can't even comprehend ? I am running windows 11 with all latest updates on both computers.

8 Replies



Any Windows updates happen recently to your PCs and your Outlook version?



Yeah. Both PCs are set to automatically download and install all windows and office updates. New updates have been installed more than a couple times during the last 10 days.

Same issue.


My OWA only syncs one accounts (instead of the 5 I've had synced for years).

Also an hour or so ago, my outlook app no longer syncs any of the other emails.

Only  my phone can get emails now. This is insane.  It's all over the web with similar issues recently.


I can't even get to the "sync" settings in OWA anymore to try and refresh. 

Rebooted a few times.  Everything updated.  



Just ended a 2-hour session with microsoft support. They used quick assist to have access to my laptop, they didn't resolve the issue. They will escalate it to lvl 2 and will get back to me tomorrow. I am starting to believe it's a problem on Microsoft's end, either the outlook server or one of the recent windows/office updates broke something. Problem is, how do we bring this to MS attention and make them work on it ?

@JParMD I have the same issue and it's across Mail clients, so it must be on Microsoft's end.



This is happening in my Thunderbird on Ubuntu Linux for about 5 or so days now, so it isn't exclusively a Windows issue.   It has to be on the server side.




It's been happening to me and another friend too.  Comes in and goes for about a week now.  We ALL wish that Microsoft will fix their servers.