FIXED!!!!
smtpd_tls_session_cache_timeout = 0
This is instantly resolved the issue
Previously I had smtpd_tls_session_cache_timeout = 604800
I noted that turning this to 0 also disabled session tickets, and I'd
read this: https://github.com/mjl-/mox/issues/237 (After searching
MailOp)
So there must be something going on in the version of Debian I have (10)
where TLS session tickets aren't working/negotiated/stored correctly.
I say this because on my Debian 12 box that was my workaround MX box
(which was able to receive Outlook messages) I have
smtpd_tls_session_cache_timeout = 604800
Anyway, that's what the issue was.
I hope this helps restore someone else in the future.
Thanks again for Postfix, and for being such a helpful community.
Tim
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