Goodbye WorkMail, hello Proton Mail

When we moved to the Netherlands and I started working for AWS WorkMail in May 2016, I migrated my personal email to this service (I'm a big fan of eating my own dogfood!), and I have been happy ever since: it is relatively cheap, definitely does the job for me [1], and knowing how it works inside always felt nice.

However, I recently looked at my recurring "IT costs" and was reminded that small amounts can add up: between WorkMail, LastPass and ExpressVPN, I'm paying 18.6 euros every month. This is not the end of the world [2] but not cheap either, so it was worth looking at what's out there.

Proton quickly became a top contender, partly because of its characteristics (who wouldn't want privacy?!) but more importantly because its Proton Unlimited bundle provides all I need at a very competitive price [3]: email, password manager, VPN and Drive (and more stuff I'll probably never use).

Migrating data

I will not talk about migrating LastPass data to ProtonPass given how trivial it was, and focus on my mail data.

I have around 2GB worth of emails, and migrating them to Proton requires

1. Changing DNS records to point my domain to Proton
2. Copying all existing emails to Proton

The first point is very simple thanks to a clear and intuitive UI; I felt surprisingly safe clicking around in Route53, and particularly appreciated the almost instant feedback about my actions.

And copying data over turned out to be super easy as well: Proton's Easy Switch tool took its time (around 12 hours) but imported everything with no issue. I really liked that the import is idempotent [4], which gives peace of mind.

Using the various products

I migrated everything one month ago, and I'm super happy with my decision.

Proton Mail

IMAP access

To maintain its security posture, Proton does not provide native IMAP and SMTP access, and instead requires running a bridge on your computer. It interacts with Proton Mail servers, taking care of all encryption aspects, and exposes IMAP and SMTP end-points on localhost [5]. These are the ones your point your favourite mail client to.

Not only does it work really well, but it's also a great quality-of-life improvement when using clients such as aerc that only have a minimal local cache, and interact a lot with the IMAP server. The bridge completely hides the latency (the server is literally your computer), and ensures a good user experience even when offline or on a flaky network.

There are however tiny drawbacks:

• If you access your mailbox using IMAP from 5 different computers like I do, each will have a full local copy of it (this is good for data resiliency though ;-))

• The bridge and the import tool work such that emails are sorted by "arrival in the mailbox", not actual receive date. This distinction would not matter if the import did not start with the most recently received emails and moved towards the past :-)

WebApp

I barely use it, but the Proton WebApp is nice: I don't miss any capability compared to GMail, and it's roughly 20 years ahead of the WorkMail WebApp.

iPhone App

Having to use a dedicated app instead of the stock Mail iPhone app did not make me happy at first, but I quickly got used to it and must admit that the Proton Mail app is much better (especially in terms of mail tagging/labelling, which I do a lot), and I would not go back even if I could.

Proton Pass

The move from LastPass is a clear improvement: all the basic functionalities are there, and I really love the aliases functionality: with the Unlimited plan, you can generate as many aliases as you want, and you don't need to communicate your actual email address to anybody. Proton automagically forwards any email sent to an alias to your mailbox, and you can protect your email address with NO usability friction.

Proton VPN

While I was barely using ExpressVPN, I'm using Proton VPN on all my devices. Performance is really good, and apart from one or two apps who refuse to work when it's on on my phone (I'm looking at you LCL), it works extremely well. And I love looking at the number of ads and trackers that have been blocked :-)

[1] I'm far from a power user: as long as I can access my mailbox with IMAP and on my phone, I'm happy.

[2] I wish I was only spending this for entertainment platforms; I should look at this next, but my kids might not agree :-)

[3] As I write this post, 9.99 euros per month when paid annually.

[4] Strictly speaking, it's not since each imported message gets labelled with a label identifying the import, but it's a detail.

[5] The bridge's security model is a good read.