By default, there is ‘accept from local for any relay’, and I’ve kept that in 
place. Is this what you were referring to?

That is what's casing the loop. "relay" looks for the MX record (Which is what you want for everting but your own domain). "relay via" skips that.


As I understand it, ‘accept from any’ would be inclusive of ‘local’—is this not 
the case?

No, I believe you are right.


As a test to understand what you’d recommended, I added

accept from local for domain <domain> relay via <server>

and tested—that presented the same mail loop problem.

1. Is <server> what you call "upstream"? Aka your mailbox system?
2. Are the accept lines in the right order? From specific to common.
3. Can you post the error log?
(4. Full smtpd.conf would be nice.)


I’m somewhat new to OpenSMTPd

Then you should skip 6.3 and move to OpenBSD 6.4, because of the new configuration style. You are learning a deprecated config style at the moment.

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