[aaron_m04]

I have this part:

> I host my own email server with Vultr on an OpenBSD VM using OpenSMTPD and Dovecot

But with outgoing mail being relayed internally to dkimproxy which signs it before being relayed back to OpenSMTPD for delivery to the other email server.

I had to set up SPF and DKIM DNS records, and one time I had to request that my IP be removed from the Abusix blacklist. Other than that, it's pretty rare for my emails to be marked as spam. Outlook 365 seems to do it much more often than Gmail though.

[zcdziura]

That's very interesting. I never thought to relay mail internally to dkimproxy. I'll have to give that a shot. I like the idea of hosting the entire solution myself and not relying on any 3rd party solutions, but relaying through SMTP2Go was the only thing that I tried that actually solved the problem. Perhaps this will offer a good solution! Thanks!

[wahern]

I also use the dkimproxy package, but there's now a third-party OpenSMTPd module that can sign messages in-line.[1] I've always found dkimproxy setup a little confusing compared to a built-in/in-line solution. I might try to switch to the module during the OpenBSD 7.1 upgrade process.

[1] I think this is the one I had I mind, though I didn't realize it was already in ports: https://cvsweb.openbsd.org/ports/mail/opensmtpd-filters/dkim...

[throw0101a]

If you run a mailing list you generally have to worry about ARC (re-signing 'chain of custody') in addition to DKIM:

* https://en.wikipedia.org/wiki/Authenticated_Received_Chain

I've found ARC to fiddle some to get going than ARC.