Outlook 2016 doesn't accept password or app password

Hi all,

I shared the reports of what you are seeing to the service team. On my test machine this morning with Outlook 2016 connected as Exchange with an app password I got multiple passwords prompts initially. I kept adding the app password and it finally took it and I have not seen any prompts since then.

If you are using Outlook 2013 or Outlook 2016 it is best to connect it as Exchange with two step verification and use an app password. This is the guidance we added to the Known Issue article too, Outlook and other apps are unable to connect to Outlook.com - Microsoft Support.

If you see the prompts persist, please post what the app is and what the connection you are using e.g. Outlook 2016 with Exchange/IMAP/POP.

Tried to re-add my outlook.com Exchange account today via my BlackBerry Hub+ Inbox account - same problem as before. Can't authenticate to the Exchange servers. Seems the issue remains. I was able to add it as just a straight up IMAP/SMTP setup but that does not help me with Calendar and Contacts sync.

I had a full day of peace yesterday - pop-ups recurring today. Still getting emails though.

I don't believe that the recent authentication issue is related to the behavior you describe regarding missing deleted items.

Using Outlook's webmail this is not an issue for me.

Using the Thunderbird e-mail client I do not have this issue but it can behave this way if not configured correctly. For the desired account under "Server Settings" -> "When I delete a message" make sure the setting "Move it to this folder" is enabled and the "Deleted" folder is selected.

Using Windows Live Mail and older versions of Outlook, the behavior you describe is unavoidable with IMAP, as far as I know, and has been an issue for some time. In this case you could try POP3.

I mentioned that earlier - until this morning, I'd get repeated password prompts with no interruption to receipt of emails. I learned to cancel the pop-ups.