Fastmail, end of an era

Apple really neglects the hell out of macOS server.

When I started this site, my email was hosted on Google Apps, then I moved to Media Temple, and from there my emails have been hosted on whatever server my website was hosted on. This was never an issue for me, and I always wondered why people hated hosting email themselves, because it’s taken me 6 years to come to a breaking point. I was pumped to finally move to a Mac mini server so I could host all my email on a Mac using Mac tools. That was quite some time ago, and it’s been chugging along ever since. Sure, it goes down when I screw up the server, but thats part of the fun.

My email gets an absurd amount of SPAM everyday — about 95% is SPAM, but my tools are aggressive in catching it. The caveat being my filters catch a lot of good email too. This is annoying, but not a deal breaker. But over the years the built in macOS email server has gotten worse, and this week it became a deal breaker for me.

I’ve moved everything to Fastmail.

Before I get to Fastmail, let’s talk about what was the actual deal breaker: inbox sync. I can deal with bad spam filtering and false positives because I was able to own the entire thing. But what I can’t deal with is showing different read counts and messages in the inboxes of my different iOS devices. Which one is right? I never knew. I could clear an inbox on one iPad, and have different states on every other device.

Pure and utter chaos. And fucking bullshit if I am honest.

At first I chocked this up to iOS betas being unstable, but it was happening on iOS 9. So I tried setting it up with the new iOS 10 macOS server accounts, and that was an even bigger shit show as I was unable to send email on my wifi, but it worked on cell. What. The. Fuck. And still things were out of sync between devices. Even worse, they would never sync back up, no matter what I tried.

So I sat down one morning and made the call which was a long time coming: Fastmail. I configured and set the whole thing up in under an hour (DNS waiting being most of it) on my iPad Pro sitting in a Starbucks.

I know of no better testament I can give than that. It was fast, they migrated my old stuff, and I didn’t require anything more than iOS to get going.

And it works. All of it. Like a dream.

I wish I had done this sooner, but stubborn people are stubborn. Email is email, and it’s nice to have one less thing to actively worry about managing, so I went ahead and paid for two years upfront. It hasn’t been long, but the spam filtering is far better on Fastmail, and well so is having a support team to contact for fixes. Highly recommended.

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