So I had an older home Ubuntu box 14.04LTS and decided to go with a Digital Ocean Droplet so all my certs would work. That worked Awesome straight away, Ubuntu 18.03 LTS and all. My iPhone was able to read and send mail by just updating the passwords (used all new passwords) but my Outlook for Office 365 is failing IMAP right off.
Aug 07 17:16:36 imap-login: Info: Disconnected (auth failed, 1 attempts in 2 secs): firstname.lastname@example.org, method=PLAIN, rip=184.108.40.206, lip=220.127.116.11, TLS: Disconnected, session=<z0Vq+I+P2I4yxAR1>
Aug 07 17:16:53 imap-login: Info: Login: email@example.com, method=PLAIN, rip=127.0.0.1, lip=127.0.0.1, mpid=18327, TLS, session=<RoeT+Y+PeI9/AAAB>
Aug 07 17:16:53 imap(firstname.lastname@example.org): Info: Logged out in=139 out=1054
I do not see much here other than it looks like it if failing Authentication, but I see the correct password being used when I unhide it… I can log into the WebMail the same way with the same password.
So this was also a bigger jump in MIAB versions for me, anything change? I followed the instructions on my new droplet admin page, they already matched my outlook setting.