Issue 31 May 21, 2023

Email service woes


If you're a long time follower of me, you might recall that I tend to return to email. Not just email as a platform and a means to communicate โ€“ I do love email! โ€“ but finding an email provider that gets the job done. I've tried many over the years, it's ridiculous. Luckily, moving between providers isn't particularly complicated if you know what you're doing. And, as you know, I run a digital agency so I'm pretty confident in these matters.

Google has the best email service, with their Apps/Suites/Workplace or whatever it is they call the business offering these days. Gmail works fine for private use, assuming you connect a domain of your own to it. After all, owning your email address and not going down with the ship if it'd come to that, that's crucial. No matter what email provider you pick, I urge you to register your own domain. That way, moving elsewhere won't lock you out from passwords recovery and the like.

Anyway, Google has the best email service. It's not the prettiest, and while I dub it the best due to a combination of deliverability and handling spam (I get a lot, my email address is old and widely published), I don't think it's perfect. It's probably better for me, with the amount of spam and junk mail I get, than it is for the average user.

Google is also reading your emails, targeting ads towards you, which, to me, is unacceptable. That's why I don't search using Google, I don't put anything in Drive nor Docs, and I certainly won't email using their service. I moved my personal email from Google years ago, but the agency was trickier. We started that journey about a year ago, I think, and haven't looked back. So long, Google. We'll keep our, and our clients', privacy, thank you very much.

All good? Hell no.

Our first stop was with Proton. This is a security first, encrypted solution for email, calendars, and a cloud drive. You also get their excellent VPN service, and lately, a password manager. The latter wasn't launched when we moved to Proton, and the whole suite was pretty new. I've used Proton's email service for years, it's solid, and setting it up for a team was easy enough. Getting it to work however, wasn't.

First, there are no shared calendars, which means that there was a lot of subscribing to calendars back and forth. This, in turn, added to communication, with things like "could you update this and that" which shouldn't be an issue. I started looking for dedicated calendar services, but that didn't feel right.

Then there was the fact that we had to use the web interface on computers, and dedicated apps on phones and tablets.[^1] While the interface is pretty solid, it's not as good as dedicated email apps. People like picking their apps too, so this wasn't helping. Meanwhile, Proton's own apps are spartan. They get the job done, but not more than that.

Security comes with the drawback that to be secure, you need to use modern technologies. You can't offer that to a user because Apple doesn't support it (yet, I hope). The same goes for equivalent on all platforms, thus Proton added additional overhead. I've got the same problem with Skiff, another encrypted and promising all-in-one suite. Email, calendar, a drive, and even a documents feature that reminds me of Dropbox Paper. There's a native app that crams this together, and dedicated phone and tablet apps, but it's the same issue: You can't pick your tools. This limitation bothers me.

I will say that I recommend both Proton and Skiff. The former has been around for a long time, and I'm a user still. The latter is young and evolving, with an open dialogue with users, which I applaud. No hard feelings, this just doesn't work for my team.

Which is also true for Hey, the email service and client from Basecamp. It's opinionated in its design, as Switch to iPad readers might remember. I checked in again, and nope, this won't work for us, despite the fact that we're using Basecamp at the agency. We can't even migrate our emails to the platform, which could be seen as a fresh start, but at the time, it just added to the list of negative things. Another would be price since I have multiple domain names that I need email for, and Hey will charge you for each one.

I'm not going to touch on every service I researched and tested. I crossed out everything that felt like a privacy concern, and in the end, I returned to a service that I burned pretty bad years ago, after giving it a go with my private email.

Enter Fastmail, another provider that's been around for quite some time. They offer email and calendar, and I think you can use them as a DNS for your domains as well (I use Cloudflare for that). Fastmail's services are not encrypted in such a fashion as Proton or Skiff, but they do employ app-specific passwords, and have the killer feature: Fastmail works with (just about) all apps. If you, for whatever reason, want to use their web interface or dedicated apps, you'll find that it and they work well enough. The apps are the best of the ones mentioned here, and the web interface is on par with the others, albeit more corporate looking than, say, Proton.

Victory, then?

Alas, Fastmail keeps missing the mark.

At first, deliverability was off, and emails were delayed. Turns out, accounts can end up on an internal watch list (or something), with no information of this being the case. This complicated things with a client for us.[^2] The problem hasn't persisted after it was resolved, but it sure left a sour taste in my mouth. The last time I tried Fastmail, they had something similar in place (a limit of 200 emails per day, if I recall correctly) for young accounts, which annoyed me a lot.

Calendar woes ensued, with lack of shared calendars and faulty invites from, I suspect, users of Microsoft Teams.[^3] But hey, at least I can use the default calendar app, right?

I wish there was a happy ending here, at the end, but I'm now looking for the next home for our email and calendars. I don't really care about features such as online storage nor password management, those things are covered, and we're small enough not to need the whole Skiff suite. Personally, I don't want to be forced into a dedicated app, it's one too many silos for something as portable as email, and important like calendars. I want to be able to use the right tool for the job, and that means that the service I employ for email and calendars needs to be versatile enough to work in whatever situation I throw at it.

This, I'm afraid, is where Google wins. All the new cool apps work with Google's offerings, and all the old and steady solutions that you've grown accustomed to do too.

I'm not giving up. The search โ€“ and woes, no doubt โ€“ continues.


  1. There's a Bridge app for macOS, at least, that syncs the emails, and calendar (I believe), to the default Apple apps, but I found it unreliable at best.
  2. Fastmail support claims that this watch list is automatic and turns off after a set amount of time, but we found this not to be the case. In the end, they removed it manually because we had "proved we were a real company", or whatever.
  3. I'm not sure why I can't get an invite to show up in my calendar, but my partner gets the same invite (to her email address) to work. At this point, I'm too tired to care.


๐Ÿ“ง One thing Twitter still does well is engaging around technical questions, like this one I posted about which email services there are. It became an interesting thread.

๐Ÿ‡น๐Ÿ‡ท Speaking of Twitter, Elon Musk defends gagging accounts during the election. Related: Official Twitter statement. Oh, and don't trust their encrypted DMs, obviously.

๐Ÿค– Did you know that there are people making money writing copy for fortune cookies? AI will take their job, at least if OpenFortune, a company that specialize in advertising with fortune cookies, has their way down the line. All of those words are making me slightly dizzy, and also, I'm thinking maybe this isn't the worst thing?

๐Ÿฅ  "Embrace change and discover new paths to happiness. Your resilience and adaptability will lead you to great success and fulfillment. Trust in yourself and embrace the journey ahead. Good fortune is on its way!" โ€” ChatGPT.

๐Ÿ“ฑ There's obviously several apps for the aforementioned, including a new official ChatGPT one.

๐ŸŽน Meanwhile, Pet Shop Boys' Neil Tennant doesn't think that AI songwriting is a sin. I was saddened by this.

๐Ÿ•น๏ธ If you're into pure retro gaming, Analogue is probably well-known to you. The pre-order for their NEC system machine, the Duo, is up now. Gorgeous, as always.

๐Ÿ’พ There's a DOS laptop on AliExpress that looks wonderful, but unfortunately features stolen code. Ars Technica has the story.

Got something I should read? Send it to me, either by replying to this letter, or tweeting to @tdh. Thanks!


๐Ÿ“š Convenience store woman by Sayaka Murata was an interesting read about being outside of society. Itโ€™s a short novel, which I like, and I recommend it.

๐ŸŽต Iโ€™ve been driving and spending time in the country house, which means rock music. Specifically Special forces by Alice Cooper, a great album.

๐Ÿ“บ Watched โ€ŒThe Banshees of Inisherin and wow, that's a weird and sick movie. I'm glad I saw it, but I do wish it'd be 30 minutes shorter, it sort of dragged on a bit.

๐ŸŽฎ Still wrapping up Breath of the wild. Yeah, the gaming topic is getting a bit boring. I did pick up the sequel but Iโ€™m not touching it until Iโ€™m done.

Spring is finally here, it almost feels like we've skipped it going straight to summer. I'm going to wrap up the weekend with a bourbon and a cigar, sans screens, just because I can. Expect me in your inbox again next Sunday. Until then, stay safe.

โ€” Thord D. Hedengren โšก

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