I Freaking Love Fastmail

I’m pretty sure that I had the most strongly positive response to Fastmail that I’d ever had to any piece of software. Sure, Fastmail is just email, but it’s a different kind of email service. It feels like it’s designed to work explicitly for me. There’s no enshittification, no upgrades or paywalled features. I don’t think I’ve ever gone from a free trial to a paying user of a piece of software so quickly in my life. Looking back at my email history, I signed up for their free 30-day trial at 6:24PM on a Saturday night, set up a couple of email addresses, and then changed to a paid subscription less than an hour later, at 7:18PM.

I didn’t really understand why I signed up so quickly until I went to a flea market and bought an old CRT TV. How’s that for a segue?

Anyway, last weekend, I went to the Silicon Valley Electronics Flea Market with some friends. It’s a once-a-month, warm-seasons-only swap meet that one of my Bluesky followers described as the place to unload all the “crap you stole from work 30 years ago”. There’s every kind of ancient computer on-hand, ephemera from the chip-making business, and all sorts of still useful retro tech, like CRT monitors and TVs. It’s the kind of place that you’ll see someone selling a tub full of stepper motors ($2 apiece) right next to someone who has 40 beautifully restored Xbox 360s ($30-50 depending on condition).

It’s one of those Bay Area fixtures—like the Musee Mechanique or Urban Ore—a destination unto itself that’s been around forever and is worth visiting just to experience. I’ve been going for the last few years, and I’ve enjoyed my trips there despite having to get up at the crack of dawn on Sunday morning and never leaving with more than a roll of Kapton tape or an apple fritter and a coffee or two.

Until this week, at least. At the last booth we hit, sitting on the asphalt surrounded by a slew of lesser CRTs, I spotted the exact model of TV that my first computers and my NES was hooked up to as a kid. In many ways, this TV is a core part of my origin story. I wrote my first BASIC program on a TI-99/4A that was hooked up to it. I discovered a deep love of video games that led to learning how computers work. And yes, it still works, complete with clicky knobs and bunny ears, and the classy walnut texture on the front that screamed “this is a great TV” in the 80s. Before I knew what had happened, I handed the seller $40 and I owned the same TV that I spent countless hours in front of as a kid.

So, that’s how I ended up buying an 11-inch color TV in 2025. I’m pretty resistant to nostalgia, so up until that moment, I was pretty sure that my time with CRTs passed when I got rid of my last behemoth Sony Trinitron monitor 20 years ago. It turns out I just needed the right one to pull me back in and get me excited again.

And Here We Are, Back at Fastmail

Fastmail made me excited about email again. That’s why I signed up so quickly and that’s why I’m writing about it today. It did it with a series of workmanlike features and a steadfast approach to usability at all costs.

You see, I’d been thinking about email the same way I thought about CRTs—as a dead technology that I’d written off. I had given up, partly because of spam, but also because the tools just weren’t improving to match the way I use email today. I don’t want or need AI writing assistance in my email client. I don’t need complicated workflow automation for customer service inquiries.

I just need tools that makes it easy for me to manage a large number of daily emails, sent to a handful of different addresses, each with its own unique set of rules, signatures, and other contexts.

This is where Fastmail shines. Unlike traditional email services—Gmail, Proton, Hey, Outlook.com, and the rest—which are designed to be used with a single email address and have varying levels of accommodations for people who use multiple emails, Fastmail is designed for people who use multiple emails on multiple domains and want to manage everything from a single unified interface.

Sure, when you sign up for Fastmail, you can register [email protected]. But it shines when hook your Fastmail account up to every domain and email address you own. And unlike every other email provider )and my domain registrar), they don’t charge me a few bucks a month for each email address I use. More on the multiple domain stuff later, but I was paying more than the $60 a year that Fastmail charges for forwarding addresses on every domain I own.

Why Fastmail Is Good

• It handles the complicated business of setting up email on your own domain. No one should run their own email server in the modern era. It’s difficult, the penalty for messing something up is that the domain becomes unusable for email for all eternity, and there’s a bunch of sticky legal stuff that comes with accepting files from random people on the Internet.

• The folder structure makes a ton of sense. You can set up basic rules on a per-folder basis, allowing for automatic purging of old emails, setting a default account that new messages and replies to emails in that folder use, and even share access on a per-folder folders with other people (with a toggle allowing you to choose whether you want to share read status on individual messages).

• Email filtering on inbound messages happens based on the account it’s received from, not the information on headers. So you can say put all emails from Account X in this folder, and then run your filtering rules on them there. This prevents emails that use bcc: or fake headers from bypassing the filtering rules you setup on your inbox.

• The clients that I’ve tested (web and iOS) are fast, lightweight, don’t have a ton of tracking cookies and other nonsense, and generally get out of the way of the work I need to do. (You can also use traditional IMAP clients if you want, but you lose access to some of the cooler features when you do that.)

• There are several ways to generate one-off masked email addresses you can use in place of your actual email in case one of your accounts gets compromised or someplace you signed up for starts bombarding you with spam. You can either create them using some basic rules (which are established on a per email address or per-domain basis) or using their 1Password extension to create a new email address when you create a new login in the 1Password apps and extensions.

• It includes a fine calendar app, which will unify all of your existing calendars into one view, if that’s the kind of thing you like.

• You all know how I feel about notifications, and I’m impressed with how they operate these. Each device has its own notification settings—and you can set either general rules for notifications (all emails from contacts trigger a notification or only emails from VIPs notify you or nothing ever triggers a notification) or you can set up rules that trigger notifications based on criteria you specify.

• If you want to use your Inbox as a To-Do list, you can snooze messages. (I still think that it’s a bad idea to do this though.)

• Their anti-spam tools provide good base level protection out of the box and a great deal of granular control for folks who have edge cases (if you want to forward all of their email from a spammy Gmail account or if you want to auto-delete especially spammy messages on arrival).

• The default migration path, which has you log in to your old account from Fastmail, will pull your contacts, calendar, and email from your other accounts and set them all to stay in sync with the old accounts, if you choose to do that.

• One click unsubscribe from mailing lists you’re having second thoughts about getting in your inbox (not this newsletter please!)

• The setup, especially if you’re using your own domains and already have websites hosted on them, is tricky and involved adjusting some DNS settings. If you don’t know, adjusting DNS settings is fraught with peril, so if you’re nervous about this, their online help responded really quickly when I asked some questions. I’m competent but extremely nervous about DNS changes, and I found their documentation to be good enough that I was able to set up all of domains in a few hours one night. (As we all know, making scary DNS changes is always best to do late at night.)

I could go on, but the TLDR is that this service is worth much more than $60 a year (but please don’t tell them that).

If you want to try it out, I have a referral code you can use to get 10% off your first year with Fastmail (Full disclosure: I get $10 when you activate your account, but I also wouldn’t recommend something like this if it didn’t kick ass).

What’s Next?

As I’m waiting for the hardware I need to connect my MiSTeR to my new TV, I’ve spent some time over at my pal Wes Fenlon’s excellent twice-monthly emulation news newsletter Read-Only Memo. Wes is a Tech Pod regular and has been doing amazing writing on the topic for more than a decade now, so I’m always excited to see a new issue drop into my inbox. PS if you don’t know about ShaderGlass but want an easier way to drop fancy filters on your old games, you should check out the most recent edition.

The first week of my paid subscription over here has gone great, despite forgetting to add the “Hey, this newsletter is reader-supported!” reminder in the post. Thanks to everyone who signed up, gave me feedback, or just sent a nice message. I’d always rather work for readers than advertisers, so if you find my work here useful, please consider upgrading.

This week’s newsletter has me thinking about all of the core infrastructure that we’ve ceded to spammers. Phones, text messages, faxes, paper mail, and email are all overrun by spam now. I feel like better tools have helped me reclaim my email, but I don’t think I have the same options on more closed networks, like phones and text messages

The place I’m most worried about spam is the web. I talked about it last week, but AI is empowering new frontiers in spam on the web, and I’m not OK ceding it to the spammers. This week I’m going to spend some time looking at the tools and techniques that people are using to excise different types of spam from their lives. If you have a favorite one, please mash that reply button and let me know

Thanks for reading. I hope you have a lovely week, and as always, if you enjoy the newsletter, please consider subscribing!