Has anyone tried Fastmail before? How is it compared to mailbox, Skiff and M365?

I use Fastmail and used to use Mailbox. I haven’t used M365 though. So I’ll just compare Fastmail and Mailbox.

I’ll start by clarifying that my threat model doesn’t need email content encryption. But if yours do, Mailbox has inbox encryption using PGP, which you can enable. Fastmail doesn’t. But since you are considering Fastmail, I’ll assume yours doesn’t either.

I prefer Fastmail primarily because of 2FA. Mailbox’s 2FA implementation is weird, as you have to append the TOTP to your password when logging in, which feels unpolished and doesn’t play nice with password managers autofill, although I guess in terms of security it’s the same. Also Mailbox seems to be more focused on you using third party clients through open protocols such as IMAP and *DAV, as they dont have smartphone apps and their webapp UI is less polished. The problem with these standards is that they don’t support 2FA. So I prefer using Fastmail because I can use their webapp and apps with 2FA so that there’s no way to log into my account without 2FA.

Fastmail also enables access through the same open protocols as Mailbox, but has app password that you can create for each individual client, instead of using the same password for all your clients. So if one of them gets compromised, you just have to disable a single app password without having to reconfigure the rest of the clients. But as mention earlier, I don’t use these open protocols as I prefer securing my account with 2FA. I would consider using these if it had more controls to restrict which IPs can use which app passwords, or setting how many concurrent sessions are allowed for each app password.

Because I use the web and apps instead of third party clients, another thing I value is the UI and UX of the provider, and I prefer Fastmail’s to Mailbox’s in all the services: email, calendar, contacts and files. Although I only use the email and the calendar “shared” events.

Also I like Fastmail’s masked email feature, which has matured a lot since it got introduced. And I prefer it over the standard email alias and wildcard implementation that both Fastmail and Mailbox have.

Edit: something I forgot to mention that you might consider important: Fastmail is based in Australia while Mailbox is based in Germany. I trust Germany more than Australia when it comes to privacy and not abusing power, but this might just be a silly bias that I have and both are probably equally awful. But that’s the main reason from time to time I’m tempted to go back to using Mailbox instead of Fastmail.


Thanks for your reply. Got few more questions :slight_smile:

  • Regarding alias creations, how is it compared to SimpleLogin? Can I create aliases easily and reply from the aliases?
  • Does it support mobile and desktop versions of Outlook?
  • Does it support shared mailboxes?
  • Can it share calendar between users?
  • Can I assign different licenses to users? Like Pro license to me and Standard to my wife?

I haven’t used SimpleLogin. In Fastmail you can create aliases, which in Fastmail are email addresses you choose, and masked email addresses, which are generated with two random words and 4 random numbers under a domain of your choosing (any domain you own and have configured in your Fastamil account or a selection of Fastmail-owned domains). You can create masked emails quite easily (there’s a button in the inbox menu). Aliases have to be created through the account settings, so it needs mocre clicks, but it’s still quite easy. You can also set up a wildcard address for a domain you own.

You can reply from both aliases and masked addresses. When composing an email, there’s a drop-down in the from section that allows you to choose one of your aliases or masked email addresses and also the wildcards you might have set up. If you choose one of the wildcards, you can type any email address for that domain, even if it’s not any alias or masked address you might have.

I don’t know about Outlook, but it does have IMAP and I believe it also has active sync.

It’s possible to share email folders with team/family members.

You can invite and get invited to calendar events through the standard, so it’s cross compatible with other calendar services like Google’s. You can also Share a whole calendar with another team/family member.

You can assign different licenses to each user in your team/family and get charged accordingly.

Completely different audiences.
Fastmail: Techy people
Skiff: Privacy
M365: Business / Enterprise.

I personally use fastmail, linked with 1Password for the masked address feature.
What made me pick Fastmail is how open they are, if they have an outage, they will tell you why, and what they plan to do to stop it, their blogs are amazing.
I’ve been using them since about Oct 2021, they had a massive outage just after I joined due to a DDoS on a few smaller email providers, they held it off, told everyone why, what happened and how they plan to prevent it in the future.

Their DNS is great, my current domain is through Fastmail directly, I manage my DNS via them anyway (I believe they use Gandi, their domains are registered with Gandi).

They are not the best for privacy however, they are based in Australia, DCs in New York, but they dont “collect” data, because you pay for it.
Again, open-ness got me to be a paying customer.

Skiff: Never used, seems like proton mail?

M365: I am an admin for this at work with extensive knowledge in Exchange, DO NOT USE IT for personal, Microsoft is horrid from a privacy perspective, every year the spam filters seem to fail, their spam filtering is horrid anyway, it requires a lot of setup for a “home” user to make it work properly, MS support for me is shocking and it’s quite expensive for a home user, the only flip side to this is if you want to learn Exchange, in that case get a dev account for free.

Out of the 3, I’d go fastmail because its easy, you can set it up to collect stuff from Gmail and Outlook so everything is in one place, their web UI is great, spam filtering is great and customisable, DNS controls are great and the 1Password integration helps, and you can have like 600 mail aliases if you so need (may aswell use catch all at that point).

1 Like