Outlook 2016 Keeps Asking for Password

@Gabriel Bratton you mentioned that Outlook Team is investing an auth prompt. Do you have a link to the thread?
Windows Security prompts keep popping up every 30secs on Windows 10 PC. Tried resetting Outlook Profile (recreated .ost, also we moved and recreated Mail Profile) - this worked until we rebooted the laptop. This issue has been ongoing for the last 2 days now.

We are using Outlook O365 Pro Plus version.This is the one is what I'm seeing:
http://woshub.com/outlook-keeps-prompting-credentials/

Downloading and installing over 65 updates did not solve the problem with the request for password. 

I created a new profile, the same as my current profile, and received an instructional email from Microsoft telling me to reconnect Outlook 2016 to my Outlook.com account. However, the link provided with the detailed instructions ( https://go.microsoft.com/fwlink/?linkid=837697 ) gives me this error message: This link has expired. Please contact the sender of the email for more information.

How do I reconnect?

I am having same issue and Microsoft phone support rep cannot figure it out either.

i think Microsoft broke something with ActiveSync for Outlook.com and isnt owning up to it.

Same issue here.  Outlook 2016 was connecting to Outlook.com email fine until last night.  This morning no mail, error requesting password.  entering password made no difference, and deleting and re-adding account is stuck in loop of 'enter password'.  If I deliberately enter a bad password then it gives an error, the right password just loops.  Confirmed password correct through web portal.

Dave

There is a service event that is causing some Basic Auth connections to fail.  I am not sure if that is causing this issue though.

Something that will help me investigate further is if you could test Autodiscover and send me the results.  I will send you both an email using the Forum Moderation.  If you could send me the results of this test I will follow up with the service team about it.  To do this test go to the bottom of KB https://support.microsoft.com/en-us/help/4495260 and run the test for "Check Autodiscover status".  

Please send me a screen capture of the Results tab such as below and copy the contents of the XML tab and save to Notepad or Word and send me that too.  I'll send you email shortly.  

When I run the test the prompt for password appears again in a loop. I managed to get the attached.

Sent to you in PM

Gabe I sent you the results. I cannot run the test because I get prompted for the password which is not being recognized.

I get a local autodiscover failed 0x8004010F