outlook 365 mac keeps asking for password

If anything unusual is happening to my small business clients with the simplest possible setups, then it should also be happening to many, many other people.

There are hundreds of online forums where Office 365 and Outlook bugs and problems are discussed in near real time.

There are millions of Outlook users with Office 365 mailboxes. In the last week, I’ve heard the same story from several more clients. Occasionally it slows down and they’re blessed with a few quiet days but then, out of nowhere, unwelcome prompts start popping up again. All of them were dutifully filling in their passwords and checking the “Remember my credentials” box, of course, but then having the prompts return over and over again. One business was hit particularly hard – many of its employees started getting the prompts over the course of a few days. Passwords have not expired and are set not to expire. There are no recent changes to their accounts. These are all users running Outlook 2016 with Office 365 mailboxes. At its worst, Outlook password prompts are popping up every ten or fifteen minutes.

Starting a month ago, Outlook began prompting a few of my clients for passwords. Feel free to look away if this doesn’t apply to you. This is a frustrating story of a poorly-defined bug with no solution.

Outlook 365 mac keeps asking for password