Interesting coincidence to see this post. I just tried setting up my account on the Outlook app (but on iPhone) and it didn’t work. Apple’s default Mail app works fine, as well as Thunderbird on desktop.
From what I’m seeing in the logs, Outlook does use TLS and plain password auth when it’s trying to log in with IMAP. The SMTP is what seems to fail —
lost connection after UNKNOWN from unknown [IP ADDRESS HERE]. If the SMTP settings fail, it won’t let you log in and immediately logs out of IMAP (you can’t see this happening, it happens in the same second).
Because of this, I tried adding Gmail’s SMTP settings instead. With port 587, it was a no go. When trying port 465, it worked.
So the issue seems to be when you try using STARTTLS (port 587). I suppose the Outlook app uses SSL (port 465), which was hard to discern since the logs don’t really say and we can’t see the logs on Outlook’s end.
Mail-in-a-Box should have the ability to use port 465 for sending, according to the In Development section of the changelog:
- Sending mail is now possible on port 465 with the “SSL” or “TLS” option in mail clients, and this is now the recommended setting. Port 587 with STARTTLS remains available but should be avoided when configuring new mail clients.
So the workaround right now is to use a different SMTP server like Amazon SES or Google Workspace. Bear in mind that this route requires extra steps, so unless you’re already using these services, it’s probably not worth setting it all up. I’d just wait until MiaB is ready to support port 465.