Outlook 2013 keeps asking for my outlook.com password

Hi, I've had the same problem. For about 6 months from August 2023, Outlook 2013 has worked without a problem using an 'App Password', however in the last week something has changed. Initially I fixed the issue by removing App Passwords and generating a new one. But then two days later the problem returned. This time using a new App password didn't work. (App passwords are explained here.)

The following worked for a while, but not for long:

1. I updated the registry as per the advice on the page 'How modern authentication works for Office 2013, Office 2016, and Office 2019 client apps'.
2. Rebooted PC.
3. With Outlook not started, I went in to the Control Panel and into the Mail (Microsoft Outlook 2013) (32 Bit)
4. Went into Account Settings
5. Picked the @outlook.com from the list of accounts and pressed repair.
6. When the repair was complete I closed the open windows.
7. Started Outlook. As Outlook was starting it gave a message about changes requiring Outlook to restart. It asked for the password. I waited for Outlook to finish loading, closed the password screen, then closed down Outlook.
8. Started Outlook again. It started without asking for a password and is connected to my account.

However, the next time I started Outlook, it again asked for a password!

So, I've tried the App password approach again, and it connected by that method. But then 5 minutes later it is asking for a password again.

The behaviour seems to be random.

Is this happening to everyone with Outlook 2013? Is there a solution?

I am wasting hours on this, it is very frustrating.

Yes, started happening to me about a week ago, across three different Outlook accounts, one from live.com and two from outlook.com. Each profile randomly disconnects and prompts for password. Sometimes entering it will briefly resolve the problem, sometimes it will just keep prompting, sometimes it's enough to click on the "Need Password" entry in the status bar to restore connectivity.

There was a similar issue in Outlook for Android a few months back, when it constantly asked to sign in, even so email was coming in and going out normally. It seemed to be caused by OneDrive integration. Once I added and signed in to each account's OneDrive in the storage account settings, in addition to the email accounts, the prompts finally disappeared. Not sure if there is something similar at work in Outlook 2013.

Olli, thanks for your feedback. After making the earlier post, things have improved. The pop up box asking for the password to be entered has stopped appearing, but every few hours I get a message in the taskbar notification area stating 'Outlook is attempting to connect to myaccount@outlook.com. If your password has changed it may ne'. (The notification box doesn't display the full message, I guess it should finish 'need resetting.')

I've been ignoring this message because Outlook 2013 remains synchronised with my account and so the notification doesn't make sense.

I haven't found a way to understand if Outlook 2013 is currently connected using an 'app password' or if it is using 2-Factor Authentication in the background.

Whilst it continues to work, I won't experiment further!

I too haven't had issues for the last 24 hours. All of my three Outlook / Live accounts are syncing and sending / receiving email normally in Outlook 2013 at the moment.

Let's hope this was a temporary issue, probably caused by changes to the authentication processes behind the scenes where someone or something temporarily affected older Outlook versions.

Unfortunately the pop-up boxes started reappearing very frequently, but only for the two out of my three accounts that are not primary. Entering the correct password doesn't seem to achieve anything. Just closing the pop-ups makes them go away for a few minutes. Clicking on "Need Password" in the status bar will still reconnect each account without prompting, which makes me think that whatever is continuously prompting for the password is a secondary service not related to email (like the OneDrive storage accounts in Outlook for Android that I mentioned earlier). Emails go out and come in normally on all three accounts, but switching folders or previewing messages takes longer and sometimes makes Outlook 2013 unresponsive for 5 to 10 seconds. Also, a banner appeared that says "We can't show MailTips right now" for the two non-primary accounts when composing a new message.