Back to Fastmail, redux

“Glitchy, slow, and inefficient is no way to go through life, son.”

2023-01-04

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A few weeks ago, I wrote what I thought would be the last installment of my multi-month, six-post exploration about whether to host my custom-domains email on Fastmail or Apple’s iCloud+. Ah, but it’s never quite that simple where I’m concerned, so here’s post #7 on this subject.

For those not familiar with the earlier episodes in this farce, here’s a TL;DR version for you.

In 2017, I began using Fastmail to provide custom-domain hosting of my email. In 2021, I added a second domain to that; and, also that year, Apple announced it would begin offering custom-domain(s) support in iCloud Mail for iCloud+ subscribers. I waited until mid-2022 to give it a serious try. It didn’t take me long to confirm the technical superiority of Fastmail but that service was an additional $50 a year, while I was already paying for iCloud+. So, in that supposed-to-have-been final post in the series, I put down my metaphorical foot and went with iCloud simply for the money-saving aspect.

As you’ve probably guessed by now, I changed my mind yet again, and brought my email back to Fastmail earlier today.

Why? Well, in no particular order:

  • I found other ways to cut expenses, more-or-less compensating for the added cost of Fastmail. At least one of them wasn’t even available (as far as I knew) when I began this whole experiment; I’ll leave that tale for another time.
  • As I kept running into things about iCloud’s IMAP setup that annoyed me (as before), I longed for Fastmail’s much better and smoother JMAP implementation.1
  • My Apple gear, all purchased years ago within the same 12-month span, is nearing a collective age which will force me to consider multiple replacements in the not-too-distant future. There’s obviously a certain degree of ecosystem lock-in when using iCloud to host one’s custom-domains email, and I didn’t want to restrict my future options more than utterly necessary. Fastmail works well with nearly every OS and device I might consider.

Incidentally: in coming back to Fastmail today, I had to start a new subscription, because I’d killed the old one last month just a couple of days before it would’ve reached auto-renewal. To save a few bucks per year (and to avoid any inflationary nastiness), I locked in for three years. So, since I assume there won’t suddenly be magical remedies for all my above-stated objections to iCloud-hosted email, it seems this really, for God’s sake, is the closing chapter of this little clambake.

. . . Well, that is, at least until sometime in late 2025. (I know myself all too well.)


  1. Moving my 27 years’ worth of email from Fastmail to iCloud usually took several days, but going the opposite direction took roughly eight hours; and it would’ve involved even less time had it not been for iCloud’s off-and-on glitchiness during the process. I was moving a little under four GiB, a little at a time as I recreated my one-folder-per-year Archive setup, via a fiber connection that generally uploads at about the 425–450 Mbps range. I used MailMate, having previously learned that only MailMate’s muscle — i.e., as opposed to that of Apple Mail — was up to the task of minimizing iCloud’s aforementioned glitchiness. ↩︎

Next: Finding and fixing an SMTP oddity on my iDevices

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