Office 365 Support?

[SlothCroissant]

I'm trying to get this working with Office 365 email (Exchange Online). Here is Microsoft's documentation on getting SMTP running:

https://support.office.com/en-us/article/POP-and-IMAP-settings-for-Outlook-Office-365-for-business-7fc677eb-2491-4cbc-8153-8e7113525f6c?ui=en-US&rs=en-US&ad=US

When I replicate this in NowShowing (Port 587 and smtp.office365.com), I get the following error:

root@NAS01:~# docker exec nowshowing combinedreport -t
/usr/lib/ruby/2.3.0/net/smtp.rb:977:in `check_auth_response': 504 5.7.4 Unrecognized authentication type [redacted.namprd20.prod.outlook.com] (Net::SMTPAuthenticationError)
        from /usr/lib/ruby/2.3.0/net/smtp.rb:741:in `auth_plain'
        from /usr/lib/ruby/2.3.0/net/smtp.rb:733:in `authenticate'
        from /usr/lib/ruby/2.3.0/net/smtp.rb:568:in `do_start'
        from /usr/lib/ruby/2.3.0/net/smtp.rb:521:in `start'
        from /usr/lib/ruby/gems/2.3.0/gems/mail-2.6.3/lib/mail/network/delivery_methods/smtp.rb:112:in `deliver!'
        from /usr/lib/ruby/gems/2.3.0/gems/mail-2.6.3/lib/mail/message.rb:252:in `deliver!'
        from /var/lib/nowshowing/mailReport.rb:98:in `block in sendMail'
        from /var/lib/nowshowing/mailReport.rb:89:in `each'
        from /var/lib/nowshowing/mailReport.rb:89:in `sendMail'
        from /usr/local/sbin/combinedreport:386:in `main'
        from /usr/local/sbin/combinedreport:394:in `<main>'

Platform: Docker running on UnRAID 6.3.3 using latest image of NowShowing.

When I was using PlexEmail back in the day, disabling SSL was the solution for this issue, but that doesn't seem to be an option here. Any thoughts? Anything I can pull for you to help troubleshoot?

[ninthwalker]

I believe this is because Office365 uses the authentication type 'login'. We currently have auth type 'plain'. The smtp auth type is just how the server expects responses for logins.

we went with plain because it is pretty common. I'm not sure if gmail works with the 'login' type. We could look into possibly changing this, but if it doesn't work with gmail, then we def won't be switching as gmail is most popular.

[SlothCroissant]

Would be great to have the option (much like PlexEmail does), but for now I've switched over to Gmail. Thanks!

[SlothCroissant]

Closing issue as resolved for now, since I'm using the workaround of Gmail.