Outlook And The Never-Ending Password Prompt

Outlook password prompt

This is a frustrating story of a poorly-defined bug with no solution. Feel free to look away if this doesn’t apply to you.

Starting a month ago, Outlook began prompting a few of my clients for passwords. It has been prompting them a lot. At its worst, Outlook password prompts are popping up every ten or fifteen minutes.

These are all users running Outlook 2016 with Office 365 mailboxes. There are no recent changes to their accounts. The company subscriptions are active. Passwords have not expired and are set not to expire.

One business was hit particularly hard – many of its employees started getting the prompts over the course of a few days. 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. Occasionally it slows down and they’re blessed with a few quiet days but then, out of nowhere, unwelcome prompts start popping up again.

In the last week, I’ve heard the same story from several more clients.

Outlook bugs don’t happen in a vacuum. There are millions of Outlook users with Office 365 mailboxes. There are hundreds of online forums where Office 365 and Outlook bugs and problems are discussed in near real time. 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. I expect to be able to search online and find an answer, a workaround, or at least some confirmation that a problem is widespread. If a lot of people are seeing persistent password prompts, there should be lively discussions online.

This problem has been spooky. Although it was causing more than one of my clients to go batty throughout July, there was almost nothing online to suggest that it was affecting anyone else. Finally this week three discussions of the problem turned up on Reddit here, here, and here. “We have around 30 workstations here and since last week some people are getting random prompts asking for the e-mail accounts password in Outlook. It happens at random times, to random people and random workstations. Entering the password doesn’t work, it just gives the prompt again.”

A few commenters in the Reddit threads refer vaguely to Microsoft acknowledging a problem with their “Autodiscover API.” I didn’t get anything from Microsoft when I spoke to them and no one seems confident that there’s a fix in the works.

When Outlook prompts unnecessarily for a password, there are a number of troubleshooting steps. I’ve tried all of these and the prompts are still happening. But if you’re an IT person diagnosing persistent Outlook password prompts, maybe this will give you some ideas. Here’s my checklist of things I’ve tried for my clients in the last month, for what it’s worth. (As always, try one at a time, then restart the computer and test.)

•  Run the Microsoft Support And Recovery Assistant For Office 365. All IT support personnel should have this page bookmarked.

•  Click Cancel on the password prompt. Outlook might immediately connect normally. If Outlook says “Need password” at the bottom, click on those words. For at least one client, Outlook then immediately switched to “Connected” and hasn’t prompted again since then.

•  Open Control Panel / Credential Manager and remove all passwords related to Office or Office 365.

•  Create a new mail profile.

•  Ping outlook.office365.com. One Reddit contributor thought the password prompts came up when pings fluctuated up to 400-500ms.

•  Add some registry values to control Autodiscover, per this Microsoft support article.

•  Install the most recent updates for the Office programs (in an Office program, click on File / Office Account / Office Updates).

•  Change the password on the mailbox.

•  Disable the Microsoft Account Sign-In Assistant service, if it’s running.

•  Do a Quick Repair of the Office programs.

A few weeks ago I wrote about a series of odd problems with the Office programs that are shaking the confidence of users. Business users live their life in Outlook. It needs to be rock solid. It should be rock solid. What do I tell employees who are being hammered with annoying prompts that I can’t fix? They’re going to lose confidence in Outlook, or me, or both. I don’t like being in this position, not one little bit.

If we’re lucky this problem will fade away and we will never know what caused it. I’ll update this article if I get more information.