Outlook 2016 doesn't accept password or app password

This discussion forum itself is having an issue. I'm seeing everyone's display name as A. User.

Anyway, in my case, I have been connected to my 365 Exchange mailbox for years and NEVER been prompted for password EVER... until today. I'm using Outlook 2016 with up to date patches. Today I see a prompt to choose if my account is Work/School or Personal account. I click Cancel (without choosing anything or typing my password). I then close Outlook and get back in. Outlook does not ask for anything. It connects just fine. It's back to normal now.

I'd be really upset if my users start getting prompts. Many of them don't remember their password. This means I have to reset many users password because of this crap.

To clarify, this is on an iPhone 13 installation when choosing either Microsoft Exchange vs. Outlook.com. The Microsoft Exchange option didn’t even recognize the server.

Same here. Tried switching back from outlook.com to Microsoft Exchange. Didn't even recognize my Exchange account, even when manually entering server.

The "senior role" thing means nothing and just comes off as somewhat pathetic to post.

Go to Google, MS doesn't care. Guess what, Google doesn't either. I highly doubt from your descriptions that your company has the user base to move the needle for either one of them.

Ironic that you accuse me of using multiple accounts here, when you and your pal are replying to and liking each others' posts right around the same time consistently.

My motivation is to tell people to stop throwing tantrums and focus on actually resolving their issue, even if just a workaround for now (and/or be using the correct settings so that when it is permanently fixed, they won't keep having problems). Simple and clear, no hidden agenda.

Following my own advice, I've seen 2 popups on my phone in the last week and both times just tapping OK made it go away (only because my phone does not support modern auth for activesync on personal outlook.com). Both my personal (3 PCs) and work outlook clients have never once thrown a prompt this whole time. There have been less new people posting issues here in the last week as well, yet you're still having all kinds of problems, so instead of arguing with my comments or making empty threats to MS, why not actually try to resolve your issues?

My Oauth mail account is functioning, but my calendar and contacts are not. And none of the suggestions you've provided are resolving the issue. My issues with TBSync were intermittent until this past Wednesday. Now they're constant, suggestion MS is making the problem worse, not better.

I really appreciate your time in answering my posts, but I again have to ask why MS hasn't just rolled back its untested changes that have caused this situation, and instead are leaving its users to flounder with a non-functioning service? It's unnecessarily frustrating for everyone involved.