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Re:How to run your own mail server (2017) by yellowapple on Tuesday November 19, 2019 @04:14PM (#21578366)
Gmail seems to have no trouble with my mailserver. AT&T/Yahoo used to, but there was some online form I filled out at one point to get myself whitelisted (it was years ago; don't remember the details) and that stopped being an issue. The main problem right now is Craigslist (which outright refuses to deliver my server's mail, so I have to use my Gmail account or stick to SMS / phone calls).

Stack: OpenBSD VM (on 1984.is) running OpenSMTPd + Dovecot + a DKIM proxy + ClamAV + spamd.

The more relevant pain point is that the VM hangs every couple months and I have to hard-reboot it from the VPS web console. Also, I've been pretty lazy about staying on top of new OpenBSD releases. One of these days I'd like to go redundant (whether with both mailhosts on 1984 or putting one on a different provider), which would make it less stressful to do OS upgrades (I could keep one host running while doing an offline upgrade of the other, as opposed to hoping the online upgrade process doesn't break anything).

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