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This does not work for me. I have installed postfix on my server. Using https and set less my gmail to accept less secure state. But still get ERROR: attempting to send a mail 534
It does not work with plainauth. I am not sure, how it is working for you. It throws unencrypted connection error. Please let me know, if i missed anything.
Error message - Unrecognized authentication type, smtp.office365.com, port - 587
If office365 doesn't host a SMTP server at smtp.office265.com, it won't just magically work. That's Gmail convention.
It works, well I did it a bit simpler, nonetheless, thank you.