Fastmail: Things I wish I knew before switching

I switched from Google Workspace to Fastmail over a year ago, and while the switch was seamless, there are certain things that I wish I had known before the switch.

First, while I was with my personal email and my company email perfectly happy with using Google Workspace, I was one of the people who would have had to pay over $2000/year to continue using Google when they no longer supported the free version. While I’m not against paying for what I use, that was over the top.

Back then, the landscape didn’t provide many options that supported multiple domains, unlimited aliases, reliable hosting, and a decent calendar. Last but not least, the price of Fastmail is decent. Hence the decision to move to Fastmail was easy.

My experience with Fastmail has been great. The service never had downtime and is fast. Emails arrive within seconds, and forwarding works without a hitch (essential for us as my company works with forwarded emails). It’s also great to know that your emails are not being scanned (I know Google says they don’t but who can verify that…).

Sure some things behave a bit differently, e.g., marking emails as spam notifies the Fastmail spam system but does not block emails (for that, you need to select “block sender” actively). The support does not always reply timely, but at least there is support, and you will get an answer eventually. However, the option to create unlimited aliases, using as many domains as you have, and especially masked emails (in combination with 1password even better) are significant benefits of using Fastmail.

There are, however, some annoying things. You have to judge for yourself if those are a deal-breaker for you.

Login is only possible with your default email-address

As mentioned, Fastmail allows you to add all your domains. You can create aliases for those domains and receive and send emails under these domains without a hitch. This all works seamlessly and is quite transparent.

The issue arises using a third-party service with their SMTP or IMAP servers. To be more precise, while you can create dedicated app passwords for each service, it’s all tied to your default email domain (user). In practice, you cannot use a third-party service with another email address than the default one within Fastmail. Unless that third-party service is smart enough to allow a different authentication for SMTP/IMAP than your email address, it just doesn’t work. From my experience, only one service out of eight worked.

This might not be a big issue for some, but the more third-party services you use, the larger the issue is. It has caused me some headaches in the past, and I’ve had to move an email domain to an additional account to use with an external service.

Google Calendar is omnipresent

Let’s call it how it is. Google’s Calendar is omnipresent, and every service in the world can be used with it.

For instance, I’ve used Calendly for my personal and company calendar booking. Switching to Fastmail ruled Calendly out. Honestly, I wasn’t too distraught about it as they raised their prices, and I was generally dissatisfied with them. However, it also ruled out just about every other alternative.

There is, however, hope, i.e., a solution. After researching and reaching out to many booking vendors, I found Not only do they integrate with Fastmail, but their whole interface and booking experience are also second to none. I have customers that congratulate me for our excellent booking site.

More Calendar annoyances

Getting back to Fastmail and Calendar, the only other gripe is that incoming booking requests don’t honor your free/busy configuration. For instance, when my wife sends me an invite from a Google calendar that she will be out for an afternoon next week (hey, don’t judge me. We keep tabs on things like that so we can plan), she marks it as “free”. However, accepting the invite in Fastmail will mark it as “Busy” for me. This caused my time to be blocked for customers to book.

Only after a customer commented on my unavailability, despite telling him my tomorrow was free, I realized what was going on. This means that one either has to create multiple calendars, which I find a headache or then must remember to edit each invite after accepting (my current solution).

I understand that these are not significant issues, and I’ve found a solution for each one. Nevertheless, I wish I had known this before switching to Fastmail.

I hope this helps someone.