Outlook 2016 doesn't accept password or app password

Hello everyone! Since January twenty-something, I encountered this irritating problem with my Outlook.com account in Outlook 2016. I though I did something wrong. So I've search every where, mostly on YouTube, to find a solution. And, i'ts like it happened to many people before! So, it's been two weeks now that I apply multiple tricks on my PC. I've changed things in the Windows registry, created new strings... you name it. Nothing works. And now, just at this minute, I find that forum with hundreds of users having the same problem. I feel much less alone now, but I wonder what arm have I done to my PC with all those "recepies" I've tried to fix it for good. I wish I've discovered that discussion before. But now that I'm aware that Microsoft engineers are working on a good fix (and don't force me into having an app password cause I just wont be satisfied with that) I will be patient and use the web mail instead. But I really hope they will go back to the time when it was working. Thanks MB

Most average users don't even know where to start to address these issues. By the posts here, most of the commenters are technically savvy, and have knowledgeable and purposeful configuration of their own devices and email clients - we know what we are doing...

Issue started on 1/23 afternoon US Pacific, the evening before I started an oversea business trip. After I completed my almost 3-week trip, the issue is still not yet resolved, yet Microsoft refuse to rollback whatever they broke. Most of my non-technical friends and relatives that use Outlook.com/Hotmail/MSN/Live mail with a EAS client are having this issue once I pointed out the problem and symptoms. Almost 3+ weeks of this, people start to realize they missed newly added meetings or tasks, and didn't get emails until many hours after the fact - all because of this issue.

Another problem that hasn't been talked about is that, at least for Outlook desktop, the password prompt dialog is drawn on top of all other screen elements, plus it will throw a Windows notification. Every time this password event prompt dialog shows up, it's incredibly disruptive to your workflow because it suddenly takes the cursor/mouse focus away from whatever you are working on. For mobile clients, this event causes a notification to be shown as well, so you getting constant alerts, chirps and/or vibrations.

I really don't understand why Microsoft won't roll back the changes on the production system, and continue to work on debugging the problem separately for later deployment.

I tried and it did not worked. It also was intermittent. Worked for one and did not for the other and now first is out too.

It almost like promo event for subscription-based Microsoft 365.

Very bad one. Maybe they are routing for MS Edge/Web access, but i have issue with web Outlook too. Some links don't work.

Jokes aside i feel your pain and frustration. I can't be productive without outlook and sinking it down is not the smart move on MS side. There is not much of journalism outcry on the subject though. Which surprises me.

I have work provided Office 365 pro and there outlook has it's own unique issues which bug me as well. Again, one of the most needed tools in office is not up to the task.

I totally agree! What keeps me in the Windows ecosystem is 1) Outlook and that fact I have decades of emails, calendar and so on all saved and backed up in PST; 2) MS gave into the Chinese government and is fully functional in China for my business trips there. Aside from Outlook, there is really nothing keeping me invested in this ecosystem.

This issue have real-world impact. My friend was dumped by his girlfriend over this... because she sent him an invite for a group meet up but it never arrived into his phone's calendar. He either missed it or couldn't find the place without the invite...and she felt disrespected. It would not surprise me if people are dealing with miscommunication issue and conflicts as a result of this problem.