Email hosting sucks

I’m done with self-hosted email.

For years, I’ve rolled a self-hosted email server, wading through the complexity that is wiring up a half-dozen open-source utilities all wobbling precariously on a $5-a-month DigitalOcean virtual private server.

Installing and configuring an email server on Linux takes the better part of an afternoon — even if you know what you are doing. There’s many moving parts, with poor documentation and complex configuration scripts. To get a working system up and running, you need to know:

• Linux
• MySQL
• UFW
• Postfix
• Dovecot
• Spam Assassin
• Roundcube (for webmail)

And that’s the easy bit.

Even if you manage to install and correctly configure this multitude of server packages, you then have to wade into the murky nightmare that is Reverse DNS, DKIM, SPF, DMARC and a bunch of other alphabet soup acronyms.

Then, even if you manage all that, the odds are high indeed your server will end up on a blacklisted server, and your emails get flagged as SPAM.

This isn’t the first time I got sick of managing email servers. About a year ago, I ditched the self-hosted email server for Google’s G-Suite. While it solved my problem, I joined right before Google hiked the price — and that in a time when the Australian dollar deflated against the USD. I only wanted email, and Google was charging me for a bunch of features I don’t use (Docs, calendar, sites etc) and several features that weren’t even available in Australia at the time.

So, with costs rising — and feeling ripped off by Google — I decided to go back to self-hosting, but I did a bit of research and found Mail-in-aBox. This open-source utility vastly simplifies the installation, configuration and maintenance of an email server. The installation script is one command on the terminal, and the utility gives you a web admin console, and even sets up DNS for you.

At first, I was chuffed — it worked really well. That is except when I needed to email readers using Microsoft’s Outlook/Hotmail service. Even though I kept my server’s nose clean, avoiding blacklisting on all the major SPAM monitoring services, for reasons known only to Microsoft, they wouldn’t permit emails from DigitalOcean’s network.

Frustrated beyond words, I switched over Christmas, but this time I’m using FastMail. FastMail is an Australian-owned and operated service that provides email hosting. And they only do email, which is what want — no more paying for features I don’t use or need. Consequently, they are cheaper than Google, and unlike Google (at least in Australia) they allow me to save even more money with annual pricing.

So far, so good. I’ve found the service to be fast and reliable, and critically I’ve had zero problems sending mail to users with Hotmail/Outlook accounts. The convenience, reliability and peace of mind I get knowing that all the horrible crap regarding email hosting, maintenance and delivery is now somebody’s else problem, is certainly worth the price of admission.

FastMail charges by user, but you can create as many aliases as you need, which I need for things like my newsletter and Scriptorium’s password delivery mechanism to my site’s members. I really like FastMail’s attention to security, with each individual app I use (iOS, macOS and Scriptorium) having a unique password that’s separate from my primary FastMail account. That way if any app is compromised, my account is still relatively safeguarded against intrusion.

I’ve used it less than a month, but already I feel like I’ve found the best solution for my needs. Still, I’m a fickle soul, and I’ll need a little more time kicking the tyres (I’m still using the trial period) before I pull out my credit card. I’ll let you know how I go as my time with FastMail progresses.