Microsoft Outlook (or other apps) keep asking for Outlook.com password? Here's what's happening

As part of my daily research into tech issues, I recently stumbled upon some complaints (1,2,3) from Outlook users who said the Microsoft app is asking them to sign in (or login) again and again using their @outlook.com password. So, I decided to dig in more and get to the root of the issue.

Here’s how some of the complainants explained the issue:

1-> For the past few months, Outlook has been prompting for my password several times a day. It usually happens when the computer has been in sleep mode, but it can occur at any time. The icon starts bouncing in the dock and I’m asked to log in again because “something went wrong.” Then I have to enter the password for Outlook to work again.

2-> I am getting an outlook password prompt multiple times a day on two separate work email accounts… has never happened until recently. Anyone know why? “Because you’re accessing sensitive info, you need to verify your password.” (Have done updates, switched it off and on again, etc)

As you can imagine, this is not the kind of experience any company would want to offer their users. So, I was curious to understand why such an annoying problem hasn’t been taken care of by Microsoft until now (especially considering some users say they have been facing this issue for months).

While reading and understanding these reports, I finally stumbled upon an MS Office support page on the Microsoft support website. This page was last updated very recently (Feb 27, 2024), and sheds more light on this problem, the underlying reason, as well as what users should do meanwhile.

The repeated Outlook.com password prompt issue – What Microsoft says?

Upfront on the page, the company makes it clear that not only Outlook users, but users of third party email services may also be affected by this “known issue.” For example, if you are using Mozilla Thunderbird, Apple Mail, Samsung email, Gmail, Yahoo, AOL etc, and facing the recurring Outlook.com password prompt issue, then this support page is for you as well.

The root cause of the problem is Basic Authentication. If your email app is using Basic Authentication to connect to Outlook.com, then you will be asked for password again and again. Basic Authentication, Microsoft says, is weak, and makes your login credentials vulnerable to being hacked. That’s the reason behind the current behavior, and that’s also why the company will be removing the support for Basic Authentication in near future.

In the coming months, we will be working to fully remove support for Basic authentication from Outlook.com, and only rely on OAuth (also known as Modern authentication).  While we understand that this experience is frustrating, we are ultimately trying to protect our customers and the safety of their accounts.

That being said, Microsoft also makes it clear that the details of this shift to OAuth will be shared in time to come. However, on the positive side, the company also shared a few measures that users can take meanwhile to fix the password prompt problem they’re facing currently. Following these measures, you will be able to update your accounts to use OAuth for authentication.

As it stands, the page currently only contains detailed steps for users of these apps: Mozilla Thunderbird, Apple Mail, and Outlook (of course). However, for all other third-party email apps, Microsoft has this to say:

Always check the add account steps to look for Outlook.com and use it if that option is available. If Outlook.com is not an option, you will want to contact the application’s support to confirm that they support OAuth against EAS, POP, IMAP, and SMTP. If they do not, you will be able to continue using Basic Auth until we announce our final deprecation dates. However, you may experience increased login prompts as we work to protect accounts.

Here’s the link to that support page.

That’s it from my side on this matter. In case this article helped you in any way, do like it and also leave a comment. You are also encouraged to use the comments section in case you have any other workaround that fixed the problem for you. Thanks in advance.