I've thought about setting up a mail server on a DigitalOcean or Vultr VPS without any experience with mail servers (for person use). Whenever I read opinions about operating a private mail server, there's usually a few people that express great satisfaction in doing so, and say that it's not too difficult. However, there are also many more people that say it's not worth the effort since there's maintenance to consider, complex setup, and the cost of email providers is usually the same or less than running your own server.

What is your opinion (or others' if they'd like to chime in)? If you enjoy running your own, are there any guides in particular that you'd recommend? Does the future of email look even more prohibitively complex for self-hosting?

Self hosting has become harder due to email abuse (spam, phishing, impersonation, etc) and the measures against this that have been introduced.

Following a guide to setup a basic email service is quite easy to do, but after a while the lack of proper implementation and maintenance of the standards will start to cause deliverability issues. Those are frustrating and most end up writing a long rant on why Google is evil because their email ended up in spam. When in fact, it usually is a misconfiguration, but those can be really hard to detect.

IMO there is still great satisfaction in running any internet service yourself. But, if you rely on this service to work, it just no longer makes financial sense to do so.

It takes resources to keep any internet service running correctly. Even the simple stuff can quickly get overlooked, I have seen so many self-hosted email servers that have expired certificates (like with the domain of the OP) or lack support for any of the modern security extensions such as DMARC or MTA-STS.

For most businesses my recommendation is not to run it yourself. Like you wouldn't run your own DNS service anymore. Of course it can be done, and in some cases it makes sense to run stuff yourself (usually when operating at a very large scale). But it almost always makes more financial sense to use a hosted email solution.

We haven't written a guide (yet) on setting up an email server with all the bells and whistles. But if you want to read more on all the email security standards, have a look here: https://www.mailhardener.com/kb/

Thank you so much for the detailed reply. I'm fairly new to programming, development, Linux, the command line, etc etc, and so am always on the lookout to learn something new. My day job is web development, but I'm looking for something that I really want to dive deep into. Email seems to be a whole universe of its own! From what you've said, maybe I'll try it once to learn a bit more someday, but for now I'll let sleeping dogs lie and keep G Suite as my custom domain email host. Thanks again!

Honestly, running an E-Mail is so tedious that I just allow Migadu to manage it for me. You have to deal with configuration (as the original poster said) and run into issues with systems just blocking you outright (especially Outlook). There are some utilities or Docker images that make it easier, but in the end its not worth the hassle. I still think domain-based email is way better than allowing G-Mail or Outlook to host your email though.

When you say domain-based, you mean using a email-hosting provider with a custom domain, is that right? I currently have my custom domain set up with G Suite for email and am thinking that's probably good enough.

I ran my own for a number of years... it was a pain in the ass and took too much time for what it is/was worth. I'm a frugal man, but it's just not worth it to me. I now have several relays pointing to my gmail and/or a custom outlook.com domain (grandfathered free account). I've thought about putting something up, but it's a headache and a half.

For delivery, if you are really just using it for personal use a mailgun or sendgrid account can allow you to handle most delivery issues, while still handling inbound.

Which still leaves the other side, actually dealing with inbound mail issues which is just painful with either too much or too little filtering. The likes of google and MS have teams of brilliant people to handle dealing with spam, and despite some little guys caught in the middle, is still far better than I could ever do on my own.

Thanks for your take on it. I'm fairly new to the world of programming, development, Linux, etc., so I'm always looking to learn things and make something of my own. A mail server sounds very neat in that regard, like building your first computer, but it sounds like in reality it's best left to the experts. I currently have a G Suite account for my custom domain, so that's probably good enough.

I don't mean to discourage anyone who wants to experiment... It's actually really interesting with a lot of options in terms of running your own. It helps to learn things from the security aspects, to the use of tools for spam, greylisting, dns lists etc. On the flip side, I wouldn't do it for my primary email again.

In the end, if you want a career in IT, or find it interesting, I'd say go for it. I've often thought about building my own end to end open-source mail service aimed at ease of administration. If I was ever rich enough to not have to work, that's one of the things I'd probably do after a few months off.

I'd suggest starting with a secondary domain and using Mail-In-A-Box on a VPS or smaller Cloud host. It's a decent starting point, and there are many other options. One of my favorites is SmarterMail (commercial, windows only though). I also ran a BBS for a number of years using Synchronet, which does email/pop/smtop and even nntp for group messages. I did have it configured with SendGrid at the time for outbound for a while, which handled delivery issues for me.

You will have headaches if you take it seriously and/or use it as a primary service without using a delivery service like MailGun or SendGrid, and even then you probably will have other headaches. My point isn't really do discourage so much as let people have a more realistic understanding. The issues the OP has are real. However, there is so much junk from bad actors that the well is poison.