simonrob/email-oauth2-proxy

O365 does not allow SMTP connections

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I have authenticated a O365 account via emailproxy --no-gui --external-auth and can access emails over IMAP, but am not authenticated to send emails over SMTP. I include links to pastebins for my emailproxy.config file and the results of a telnet session to localhost:1587.

Wondering if something has changed for the authentication flows / URIs or I am doing something obviously wrong?

You need to actually authenticate your SMTP session. Unless the telnet session is significantly redacted, currently you're trying to send email without first logging in...

Ah, it was a problem with the version of aerc (command line email client) packaged for Debian 12 (0.14.0), it abruptly closes the SMTP session after the second EHLO round. All fine on Manjaro (0.20.1-0-g2ecb8770224a).

Thanks for the advice, should probably have read a bit longer on the "using telnet to test SMTP" page! 😅