[aaron_m04]

I run a personal mail server on OpenBSD and I love it.

The one big problem I've run into is sending emails to mail servers running the Proof Point blocklist. They have my IP blocked, and there seems to be no way whatsoever to get it unblocked.

Maybe you need to have an enterprise account with them for them to even listen to you.

[daneel_w]

I, too, have issues specifically with recipients sitting behind Proofpoint setups. My IP isn't blocked per se, it's just not "trusted" because I don't send enough, so it's permanently stuck in "new untrusted sender" purgatory. I can't even return responses to e-mails that were sent to me from behind Proofpoint. At this point I consider Proofpoint a completely counterproductive piece of garbage product.

[mekster]

Why not use SendGrid/Postmark or some other delivery service and forget about using a random untrusted IP.

[daneel_w]

I prefer as few middlemen as possible for my personal communications, and not having to spend a hundred bucks a month on it.

[mekster]

Where did you get the idea of $100/mo? SendGrid has 100 emails per day free tier and PostMark has 100 free emails per month and basic plan is $15/mo.

If it doesn’t work without a middleman then it doesn’t make sense to run your own service. Any spammer can rent a server the way you can.

[daneel_w]

That's their cost for a dedicated "clean" transit. At $15/mo you're just sharing tenancy with everyone else, using their SMTP setup together with everyone else. I'm running my own setup for a handful of domains, my own configurations, signing procedures, filters, features, aliases and catchalls etc. Incidentally almost all spam I receive comes in via Gmail, Yahoo and Hotmail.

[mekster]

What matters is how inbox providers look at the source IP. At least delivery services have higher chance by filtering obvious outgoing spam than a rogue server IP.