Ask HN: The middle ground for email self-hosting?

Nowadays, I just use mailcow (https://github.com/mailcow/mailcow-dockerized) for the setup part and have a much more polished experience. Email deliverability is not a problem. Generally, you just have to make sure to correctly setup DKIM/SPF (and DMARC) and check if your IP is on some blacklist. You can get it removed easily. (Edit: Also required is forward-confirmed reverse DNS, see below).

There was one provider that denied incoming mails from me, even though I got the IP removed from every blacklist I could find. I wrote a short mail to the admin contact and got told I had to host a web page with contact information on the same IP. Since being whitelisted there, everything works like a charm, couldn't be happier.

Incoming email to my domain is forwarded through Cloudflare's free service to the generic Gmail account.

This seems to pass all quality checks to avoid being sent to spam.

Interesting. Was that just to prove to that particular provider that you, the emailer, own the domain? Or is it some more widely used (beyond that provider) practice?

Obviously GMail is such a giant that email providers have to be very careful when blocking it, but enough spam comes from there that receivers clearly use some heuristics to block some of it. I’ve even received multiple rejection notices because the GMail server my email was sent through happened to be on a blacklist!

I switched last year to sending directly from my VPS. It was partly for privacy from Google, but moreso so I could enforce outgoing TLS. For the first few days they went to spam boxes or moderation queues, but I made sure they were rescued, and ever since I’ve had no deliverability issues sending to Google, some local ISPs, and even Microsoft (which seems crazy, as I never got a mail from my domain to show up in Outlook when I was relaying through Google).

I can only speak for my own experience, of course. But that is what I experienced.

You can self host mail alongside gmail/outlook on your own domain. More than one email service can run concurrently, without any problems.

That often overlooked fact allows you to quickly set up something like gmail on your domain, then use the trial period to see if you can self-host with any success. If you can, then you can shut down the trial, or move on to trial another paid service like 365 while you're still "trialing" your own host.

It really helped me make the transition.