Ask HN: Self Hosted vs. Gmail / Outlook?

I have been setting up mailservers since the '90s when you still had to deal with sendmail's configuration format. I've used most email servers available on unix platforms. And I'm also someone who wants to do everything myself and not depend on anybody else if I don't have to. Still, and it hurts me to say this, it might simply not be worth your time. I use a paid service for my main mailbox now.

I have a mailserver handling some personal email, but I feel it's too risky (to take the responsibility) and too much effort to host email accounts for just a few other people. You can and probably will be every once in a while blacklisted by one of the big providers or have legitimate email bounce, even if you have SPF, DKIM, TLS and your own spam filters set up. You also have to keep an eye on your servers to see if no new filth gets through. And you'd probably want to keep a backup relay ready. You have to provide ways for the users to configure or fine-tune their individual spam settings and mark messages. You most likely want to install a web interface next to the IMAP and/or POP service, which opens another can of worms.

I feel I'm too old now – meaning I have so many other responsibilities – that I don't want to babysit something that is after all rather crucial and should "just work". If you have the energy and time, please go for it, otherwise just search for a reliable paid service.

Note that assuming privacy when talking about email, even though most protocol interactions might be encrypted these days, is in my opinion somewhat misguided. Don't use email if it's truly private. Or use end-to-end encryption, such as PGP.

There might be a hole in the market for a company that helps geeks host reliable email servers, for those that want more control than just an IMAP account with sieve support, but maybe the margins are too low and fighting spamming subscribers too hard.

I chose Google GSuite to avoid non-delivery of emails which was happening when I was still on self-hosting. Most emails I send used to be marked as spam and blocked. Not anymore. Fee I pay every month is very low compared to the time I used to spend managing my own servers.

That's what I use. Works great and I've only ever had a few hours of service interruption.

One alternative I would suggest to people trying to decide between self hosted or hosted email is to consider a hybrid. Host your own inbound SMTP, but use a service for outbound, e.g. Mailgun. The hardest part of running a mail server today, is getting your email accepted by the receiving SMTP server.

I run Postfix & Dovecot (with SPF, DKIM, DMARC, DNSSEC, TLS) from my home network with a remote backup just in case it goes down, as well as my own DNS servers.

I had to ask my ISP to disable some rules on their end and pay a fee to have a static IP address, but overall it was pretty painless. Though I can imagine some providers being much worse.

After the initial hurdle of setting everything up in my experience everything went mostly fine. I had to whitelist my domain on Microsoft's site, but Gmail and Yahoo worked fine from the start. I haven't had a problem since. My university teachers receive my email just fine, so did my co-workers before I was given a corporate email address.

Is it worth it? Maybe not. It was more of a learning experience for me, but I find it works just as well as any other provider I've used. At least for now.

As others have said there are lots of outdated guides. I found the Archlinux Wiki and the manpages to be the most useful resources. Also please stay up to date on the software.

I'm really happy with https://www.migadu.com. i just converted to paid. It's nice to be able to add users and domains without a price change.