Outlook 2016 doesn't accept password or app password

Hi all,

The service team implemented some more updates over this past weekend 2/10/24. The changes should be rolled out now so hopefully that will help. I'll continue to monitor and share your feedback to the team.

Since the issue primarily affects basic auth, if your app offers OAuth as an option, try switching to it. Outlook 2013 and Outlook 2016 only offer basic auth. There is a New Outlook that supports modern auth and its free but with adds, Outlook for Windows - Microsoft Apps. If you want to test it, New Outlook can be installed side by side with Outlook 2013, Outlook 2016, or any other version. New Outlook will replace the Windows Mail App and will be the same app that eventually replaces Outlook Desktop in M365. If you have an Office subscription add your main subscription account to New Outlook first to avoid adds.

I agree with others above regarding this problem not "Resolved", and note that perhaps there's some setting or error-checking function that's causing these issues. We have two iPhone 13's and two recent model iPads, and only mine are impacted. I've noticed that using the Microsoft Exchange option on the iOS email set-up (vs. the Outlook.com option) includes the "Automatic Reply" function which appears to hang ("Loading"), and often results in generating sign-on errors and/or losing data (Calendar entries, Contacts, etc.).

Why the status of this issue has been marked as "Resolved"? This issue has "NOT" been resolved at all.

Since around January 23th, every time I open Outlook 2013, (2FA enabled + app password with an @msn.com account) it prompt me with the Windows Security Outlook password prompt, if I check "Remember my credentials" it doesn't accept the password at all and keep prompting me in a loop, if I leave it unchecked, after 2 or 3 times it accept the password, but then it start asking for the password again randomly.

For some reasons, by clicking "Need Password" on the status bar connects the account to Exchange (even after if I haven't entered any password and canceled the password dialog....) but then again, it start prompt for the password randomly, rinse and repeat. The password apparently is not saved, not accepted or both or who knows what...

I'm using Outlook 2013 Professional Plus, since it was working perfectly fine until now (funny enough it works perfectly fine with all my other Gmail accounts but not with an MS one...), I also have a license for Outlook 2016 Professional Plus (that is still fully supported by MS) which is useless, since also this version is affected by the same issue.

This issue is extremely frustrating, and it's going on for almost a month now, it is supposed to be "resolved" but the fact that it is obviously not resolved and that MS is still unable to fix it (or cares to), makes you really think about what is going or not going on...

2FA is enabled - I believe it now has to be to enable app passwords to be generated?

02/11/2024 ~2PM PST Works intermittently.

After several days couldn't get it connect even with new app password, today it accepted new app password, updated all folders, but less than an hour later it prompted for password again.