Outlook 2016 doesn't accept password or app password

Question

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

Answer 1

I am not aware of any Outlook.com report that will show Classic Outlook sign ins. This is good feedback, and I will share it back to the Outlook.com Team. The M365 Admin Center will show client activity including Classic Outlook in some of its reports e.g. https://admin.microsoft.com/Adminportal/Home#/reportsUsage/EmailClients. 

Since you are getting the Windows Security prompt there must be some residual in the Outlook profile for the basic auth credentials. This might be difficult to isolate and fix. I know creating a new Outlook profile is a hassle but if you get a chance, please try that and see if it still has the prompt.

Answer 2

No. It's the normal Outlook dialog that looks similar to the ones on the older Outlook version that prompts for authentication. The one you showed is the OAuth/OAuth2 prompt, which I recall I got when I added the account to Outlook. It's not the prompt I am getting now. Plus, the logging session shouldn't time out, so I really shouldn't see this dialog.

Outlook is activated and logged into my work account, which is also the main account listed under "Account Settings".

Connection Status Dialog shows both accounts as having "Bearer*" under Authentication.

Profile was already rebuild recently due to another Outlook issue and that was from the support runaround I got. The "Report Phishing" button disappeared for over 2 months. Support was clueless until it was escalated after 2 months of back and forth. Turns out, the removal was due to Report Phishing being EOL'ed and moved to a new method of doing Report Phishing but no article was published about that.

By the way, where do I got to see active logged in session into Hotmail/Outlook accounts? I can go to Outlook Web->Setting button->search "Mobile" and find my phone listed as one of the connected session/device but I don't see my Outlook desktop as listed. If I goto my MS account settings and security, login history, all the history I see are related to Outlook Web session and does not include Outlook for Android or Outlook for Windows.