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I have this problem - Outlook 2016 doesn't accept password or app password - and i think it is a growing World wide Microsoft problem :-(
See also here: https://www.reddit.com/r/Outlook/comments/19dx64p/outlook_2013_windows_10_suddenly_not_accepting/Outlook gives me this: (startede yesterday)
I have 2 PC's with HOTMAIL accounts in Outlook 2016 ...
They both have this error.
I do get mails ... but I can´t send mails. Yesterday it did work for 1-2 hours ... but right now the error is there all the time :-(
Please help me.
Thanks in advance
Pierre
Using classic Outlook for Windows in business environments
Locked Question. This question was migrated from the Microsoft Support Community. You can vote on whether it's helpful, but you can't add comments or replies or follow the question.
In my case in Italian it does not have the writing Bearer* but Not encrypted*, what does not encrypted mean? Am I using modern authentication?
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It happened to me only once. I've been using the same Outlook 2016 since 2020 and never got a problem with it.
This year, my Outlook 2016 on Windows 10 suddenly prompted me for password. Nothing's changed recently (no password change). I clicked cancel, exited Outlook and relaunched it. Things went back to normal. It hasn't happened again since that day (a few weeks ago).
As a side note I had a problem configuring Outlook 2016 for a new user. It just wouldn't connect to the mailbox. I spent several days troubleshooting which includes adding registry entries (meant to be for Outlook 2013) although I knew 2016 didn't need it. No dice. After a few days, my user retried connecting Outlook 2016 to her mailbox and bam... it worked. I haven't made any changes on user's PC since the previous failure (unable to connect to user mailbox). That makes me believe there's something going on on the back end. Who knows what it is.
So should I resign myself? Outlook 2016 won't support this blessed modern authentication? I checked everything and more, the registry keys to enable modern authentication, they are all enabled. I do not know what to do.
In your case, are you having problems with the password request we are discussing?
Authn column should show Bearer* (English version, connected to 365 Exchange mailbox)
It's not very clear, but at the following link: https://learn.microsoft.com/it-it/exchange/troubleshoot/administration/modern-authentication-configuration
it is said that Outlook 2016 supports modern authentication, in my case, by looking at the Outlook Connection Status (image below), can you understand if using modern authentication (OAuth2)?