Windows Security wants your Outlook password (over and over) - SOLVED

Scenario: Outlook on your Windows 10 PC has stopped working. It continually asks for your username and password, but nothing you type will work.

You rarely want to see this, particularly on a busy day

You've tried Googling it. There is lots of advice about resetting Profiles, deleting Credentials from Windows and so on. Much of this is scary and time-consuming. Most of it doesn't work. And you need to get your work done. What should you do?

Ask yourself this: Did you recently change mobile phones?

It seems like an irrelevant question, but if you use two-factor authentication (2FA) with your Office 365 account there is a direct connection.

When you change phones you probably had to set up your 2FA authentication application (or at least preferences) again on your new device. You've got Office 365 running well on your new Android/ iPhone kit and all is well. Possibly even your Mac computer and iPad are also still working OK. So why not your Windows 10 PC?!

It's all about application passwords

Outlook on Windows can't handle 2FA at all well. In fact, it doesn't at all really. You have to create a special password that will work on devices that don't support authentication apps, SMS verifications and so on.

This special password is called the 'application password' and you've set it up in the past and probably forgotten that you did. And maybe that password is no longer in use, because that's what's happened to me twice in the last year.

The solution is to log into your Microsoft account, choose Security info (Update info) and Add method. Choose App password from the dropdown list and generate a new one. Call it 'Annoying Outlook' or similar, and copy and paste it to the Windows Security credentials pop-up when you next see it*.

Choose App password to make Outlook work with 2FA

If that doesn't solve your problem then you might have to rebuild your Profile, delete Windows credentials and other horrifyingly time-consuming and productivity-killing tasks. But hopefully this little tip fills the void left by robotic advice-givers on the various forums.

* Probably when you're trying to do something else, more productive.