How To Choose An Email Service Without Going Insane

It’s official - I have spent waaaaay more time (more time than a sane person would admit) investigating the best email platform for me at this moment. I am on a roll deGoogling, and have been for well over a year. Gmail was one of the first ones out. However, this left me in search of an email service I could be comfortable with. I have passed through, tested, used and left the following services (in no particular order that I can remember):

I have downloaded probably every email program (Canary, Spark, em, Edison, etc) from the App Store, and removed them.  I previously commented on some email services; some opinions have changed. I still do not feel quite comfortable with my current service (returned to Proton). Here’s an update on what I previously commented, in the hopes that writing it out may help me actually come to some sort of definitive conclusion:

Postale.io

This is the first service I used for my very own domain name email, leaving Gmail behind. Nothing but good things to say. Great price for basic email needs & unlimited custom domains. I left mainly because I wanted more options and ideally a beautiful and free native mail app, which they don’t provide. They redesigned their website and admin portal recently but still use the ugly-as-sin Roundcube webmail. As my email solution needs to cater to family members of different tech levels, intuitive and “pretty” are important.

Proton

Had Visionary, loved it, left because of the price. Later returned; still love the service. The more I have looked into email security the more I come to realize (like many) that:

1. Email is not secure by nature.
2. Encrypted email loses some of its power the moment I send an email to a less-secure service (like Google). Everything I send (and receive) from a Gmail address, for example, can be accessed through the other person’s email. This article says it all: Google Has Most of My Email Because It Has All of Yours ( https://mako.cc/copyrighteous/google-has-most-of-my-email-because-it-has-all-of-yours ).

So the big question is - if encrypted email is only encrypted if you communicate with other encrypted addresses only, is the high price of encrypted email services worth it (at present). Like the company, love the product. Not a fan of the pricing, but mostly because we don't need most of the services. An option for multiple domain evade email plans (like Tuta) would be great, but not going to unlimited just to use 3 domain names. The Family plan is almost perfect but 6 users, yes. Only 3 domains.  Really?  6 domains on Family plan at that pricing and I think it’s correct.

Tuta

I like Tuta’s approach to developing their apps and system on Linux, so all systems get the apps at the same time. The security story they’re selling is also great. Pricing is also better than Proton, if you’re just looking for email (and calendar).  The app is not ugly. It is very minimalist though.  I am not personally a fan that, when you change paid plans, they automatically bill you for the new plan, and then “refund” you for the old one. Reddit is full of people confused about this; take a look there if that is a concern.

Infomaniak

Ok, so you will go to their site, see what they offer, see their prices, and you will be very interested. As I was. I circled back around on this one many times, mostly because of the price. And there’s a LOT of information. Then, once the info was read, I had questions, so I emailed support. This is where it gets ugly. Two main pain points here:

1. I would on average wait 10 days to receive a reply
2. The reply I received would not address and answer completely the questions, which were clearly expressed.

They have a very strange setup where, if you want to use multiple domains for email addresses, one domain is the “main” one, and the other domains are simply “aliases”. This is super annoying when trying to set up different emails on different domains for different users. Of all the companies listed here, it is the ONLY one using this odd setup, and they can’t seem to explain it well. It’s not a “European thing” either, as many other companies there are able to explain their product well.

Purelymail

Great setup, easy, really reasonable pricing ($10/year) for unlimited space, domains, email accounts. Backend is ugly as sin, and if you are not proficient in setting up DNS records, this is not for you. You’ll also need an email app, if that’s a concern for you.

MXRoute

I hopped onboard this one for about a year, due to its low price. They offer an email app that is even customizable. But it’s based on Google’s Material Design, so if you are in Apple’s world (as I am) and like how Apple designs apps (which I generally do) then this app will be yuck.

Fastmail

Fastmail offered a Family plan, which was a reasonable price. Setup was nice and quick. I can't really think of much to say. I did not like the mobile app because of things like Notes, Calendar, Files, being there, and there is no function to remove them. So I moved on.

iCloud Mail

I really wanted to like this one. I really do. Multiple domain emails are possible, but just can’t get behind the idea that all your email addresses are really just an alias for the iCloud email address.

Fastmail

Ok, so during this entire investigation, I circled back to check on Fastmail a couple of times. In all of this, they did not have the cheapest nor most expensive service. Price was reasonable. Once I came to the conclusion that completely encrypted zero-knowledge email was not a need I had I checked back in with them. Right around this time Fastmail made a (controversial if you are on Reddit) redesign to their inbox. But in this update, they added an option to add or remove the services you want to display at the bottom of their mobile app. As stupid as it sounds, this was a deal-breaker the first time around; hated having 6 big ol icons at the bottom of the app, for 4 services I didn’t want to use. Now I can just click and hide what I don’t want.

Finally after an eternity of decision-fatigue, I pulled the trigger and we’re back at Fastmail. It’s all there, easy to set up, and fast as fast can be.

Masked Email / Aliases

I’ll just briefly add this note: Fastmail provided integration with Bitwarden and 1Password Keychains to create masked email addresses. However, during my second time with Proton, I got into Proton Pass and their way of doing alias emails more. So sticking with this one, but getting the subscription through SimpleLogin (which includes Proton Pass), rather than through Proton Pass (which includes Simple Login).

But that’s a post for another day (maybe).