Hello Mailoppers,

I might have asked this before but I've been going round and round with
Microsoft tech support on SMTP basics.  Microsoft has, no joke, been
working on answer this questions since June 30th.  It's been a very bad
shotgun approach of sending random knowledge bases, doing screenshares,
watching their interface crash, etc.

For years, we used to relay mail from m365 through our on-premise
Linux-based SMTP server using basic plain SMTP AUTH.  At some point,
they removed it but can't say when.  They really have no record it ever
worked other than the fact that we have the relay in place on some
accounts that back in June stopped working. 

Does anyone know what authentication methods might work with m365?  Ever
seen a KB or anything about it?  I am sad to say they are recommending
things like allowing all of their IP range to relay and the very nice
tech who is helping is just too junior to understand how bad an idea
that is.

Regards,

KAM


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