I've been running my own email server with exim and dovecot for 20ish years, I like the freedom it gives me but I have to say it's a significant investment. Not so much keeping things up to date but instead making sure that my emails are actually delivered. I've eventually switched to using fastmail just for sending emails and even with that, I don't get perfect delivery.

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mrighele 16 hours ago | parent [-]

Last year I started self hosting my email. I found that once you setup the “usual suspects” (DMARC, DKIM, SPF…) outgoing mail works without issues. In fact it works now better than the (small) provider I was using before.

And setting them up properly is not even that difficult nowadays

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groomlake 16 hours ago | parent [-]

Whenever HN discusses self-hosting email, half the people with self-hosting experience say they never had any issues and the other half says they had so many issues they had to give it up.

I self-hosted for years and I did all the standard things you're supposed to do, but I had tremendous problems with Gmail and Outlook. Other providers usually went through without issue.

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mrighele 15 hours ago | parent | next [-]

I guess there is a certain amount of luck in this, probably related to the provider, or the range that your IP reside into. (I guess google and microsoft keep their own blacklists, regardless of what public blacklists say). I wonder if the best course of action in that case is to just spin up a new server on a different provider and try again.

FWIW, in my case, I am running the server on Hetzner, even though is supposed to have a bad reputation, but I have been using its IP for more than 10 years for other things (web server, personal services etc) so I guess that helps

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weavie 15 hours ago | parent | prev [-]

How much of this is just down to your mail server being randomly assigned an IP address with dubious history or not?

	▲	groomlake 15 hours ago \| parent [-]
		Hard to tell. My server's IP was not on any public blacklists (confirmed by https://multirbl.valli.org/) and it was whitelisted on DNSWL.org at medium trust level.