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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.
Two @hotmail.it accounts I couldn't add/configure on Outlook 2016, by setting the Google servers I was able to add/configure. But now when Outlook 2016 starts, there is still the problem of the random password request. So the problem is not 100% solved.
AnotherBug - Yes OAuth is indeed supported for EAS against outlook.com/hotmil.com. As I mentioned before if a developer wants to support that, they would need to do work. It is also totally possible that they did the work to support it for the work accounts, and not did it for consumer outlook.com accounts. That would be a question you need to direct at Google or your client of choice.
I can speak to the outlook.com service that OAuth is indeed supported, and as mentioned gave two clients that were working (Apple and the thunderbird client/add-in).
The account add problem is a hit and miss situation to start with, so I am not sure if the DNS change truly made the difference, so just by chance aligned with the server started to work again.
I have used most common DNS servers and it doesn't make notable difference. I just changed my phone's device level DNS to Google's and it didn't make a difference to improve EAS-based use cases.
@v-bmyers,
Outlook 2013 and Outlook 2016 only support basic auth connections to Outlook.com. The Outlook Team never backported OAuth support for Outlook.com. As noted in the article the Outlook.com Team is tightly restricting basic auth connections due to abuse from some bad actors, Outlook and other apps are unable to connect to Outlook.com when using Basic authentication - Microsoft Support. There are no plans to make basic auth work better. Instead, the Outlook Team is optimizing for OAuth/Modern Auth since it's a more secure connection. Basic auth is already deprecated in M365 and will be deprecated in Outlook.com soon. The best thing to do is to move to an app that supports OAuth. A free option with ads is New Outlook which the Outlook Team is working on. You can install it on the same machine as Outlook 2013 to compare, Outlook for Windows - Microsoft Apps. Or, you could use Office perpetual or Office subscription to use classic Outlook Desktop.
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)?