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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