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I'm trying to configure monit to send emails through Office365. Here's the relevant configuration:

set mailserver smtp.office365.com port 587 username "username" password "password" using tlsv1 with timeout 30 seconds

Unfortunately, it doesn't work. Here's the relevant error from /var/log/monit.log:

[PST Feb 27 06:40:48] error : Sendmail error: 534-5.7.9 Please log in with your web browser and then try again. Learn more at

(Yes, the error is truncated.)

The credentials are correct - I've successfully used them to log in to Office 365/Outlook. I've also used this account to send mail through a Rails app, so I'm assuming the configuration issue is on Monit's end, and not Microsoft's.

It seems someone ran into a similar roadbump here. While I can't find any documentation confirming that Monit supports TLS v1.1, I'd be surprised if it didn't (the spec is 8 years old now).

Is there something I'm missing?

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Are you sending from the O365 email address too? Did you follow the technet article on this? technet.microsoft.com/en-us/library/dn554323.aspx –  TheCleaner Feb 27 at 20:51
    
I am, and yes, I followed that article. That's how I got Rails to send email properly. –  nsxt Feb 27 at 21:42
    
OK, I could have helped on the O365 side, but you are probably right then that the issue is with Monit. For instance: stackoverflow.com/questions/22013679/… seems to have the same issue but probably not with O365. –  TheCleaner Feb 27 at 21:46
    
Well, after having changed nothing, here's a slightly different error: "[PST Feb 27 13:49:07] error : Sendmail error: 504 5.7.4 Unrecognized authentication type" Sounds like that's more O365-related... –  nsxt Feb 27 at 21:51

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