Outlook office 2016 keeps asking for password for my personal email but not for my company email.

Chalk up another user with exactly the same problem. I feel your pain. Started happening for me at same time as you. All the symptoms and attempts to fix are identical for me. I too have moments where I think it might be resolved only to reappear. I thought I had it licked when I started Outlook in safe mode and removed all add-ins. Worked for a while, then came back. Very frustrating indeed. I almost feel as if this started when I mistakenly told Outlook to automatically enable updates. I could be wrong, but that seemed to be the trigger.

The weird thing is Google GMail works just fine in my Outlook 2016, it is ONLY accounts with various Microsoft email accounts that cause my issues.

Makes me want to switch my life from the Hotmail account i've had for 2 decades to GMail for everything but I have allot of things linked to my Hotmail email like doctors, banks, 2nd factor 2FA Verifications, Etc.

It would be a pain in the butt to switch everything and then there's that one thing I forget about that causes an issue.

The situation is still not any better. I get two versions of admin security pages when changing my app-password, these two version are random everyday. Also it's not possible top retrieve an app password, only to generate a new one

It's been 3 months of headaches and the password issue is still not resolved for my installs either. I've had to copy and paste the App password from a text file for I cannot memorize the App Password and Outlook still prompts for password two (2) times when opening and then shortly later prompts for the password again. the 3rd prompt for password I've been able to close the dialog window and then click the bottom text in Outlook that says ""Need Password", it usually connects after clicking the "Need Password" but minutes later prompts for password all over again. sometimes it works by clicking the "Need Password" but sometimes it does not and I have to use the Copy-Paste from text .txt file method. The need for the text .txt file causes a security risk.

The Microsoft Support on Twitter keeps telling me to go to Microsoft's support website and open a ticket. I've told them it's not an isolated issue and opening a ticket one user at a time is not the answer.

Quite frankly I don't have the energy to want to deal with Microsoft's idiot technical support people who give you a different answer every time based off scripts they are reading from.

The sad thing is I've not found any articles of Microsoft acknowledging the password issue since their last post I saw at the end of January 2024 where they claimed to have resolved the issue.

has anyone else found any newer articles from Microsoft related to this password issue?

Interesting articles?

https://www.zdnet.com/home-and-office/work-life/office-2016-and-2019-users-wont-be-cut-off-from-microsoft-365-back-end-services-next-year/

https://www.pcworld.com/article/2306701/microsoft-is-discontinuing-support-for-office-2016-and-2019-what-users-can-do.html

I just noticed while Outlook 2016 was open, and it said in the bottom right corner "Connected to Microsoft Exchange", the "Windows Security" password prompt dialog window popped up. I scratched my head wondering why it would be prompting for a password if it is already connected..?

As a test I sent an email (1st) from my Gmail account to the Hotmail account that the dialog window was prompting for a password. Interestingly the sent email came in to the Inbox for the Hotmail account without my need to enter the password.

I tried to reply to the email from the Hotmail account to the GMail account and the email was stuck sitting in the Outbox.

While the reply email sat in the Outbox, not being sent, I went to my GMail account and sent a 2nd email to the Hotmail account. Again the email came into the Hotmail Inbox like the first one did, all while the 1st reply email stayed in the Outbox not being sent.

I then sent a 3rd email from the Gmail account to the Hotmail account, and that too came into the Inbox of the Hotmail account, all while the first (1st) reply from Hotmail back to the GMail sat not being sent in the Outbox.

Hmm ..? What's happening with that? Any ideas?

Emails come in, but nothing leaves. After the 3rd email test that came in from the GMail to the Hotmail account I finally Entered the password into the dialog window for the "Windows Security" pasword prompt. After entering the password, the reply email for the 1st email from Gmail was sent from the Hotmail account.

Does Microsoft's Exchange configuration for Hotmail in Outlook 2016 have a Incoming and Outgoing Server name somewhere?

When configuring the Hotmail account originally the setup never prompted for Incoming or Outgoing server names, and just Auto Configured itself to connect to Microsoft's Exchange services. It is like Outlook is waiting for credentials for Sent items, but not for Recieved items?