TL;DR tried to leave Gmail for Proton Mail, but ended up running them both simultaneously which created a mess. Later added Proton Pass over Bitwarden and SimpleLogin, but run into autofill bugs and a growing sense of vendor lock-in. I’m planning to consolidate everything into Mailbox.org, Bitwarden and either SimpleLogin or Addy and use a personal domain this time to avoid being locked in again. My fumble was never fully committing to one solution.

Sometime in 2018 I wanted to get off Google (Gmail). I did research and created a Proton account. I imported all my email from Gmail to Proton. It looked good. I bought a domain name, attached it to Proton, redirected all future Gmail emails to Proton to catch them all and update the addresses in the services that I use. I was also using Bitwarden at the same time.

After a few months I needed to look up some purchases in my email archive. I couldn’t find them. I was doing it on my Android phone. I tried various combination. I KNEW what I bought and the keywords to find it. It was not there. Did Google lose my email?! Was I going crazy? No, it’s just that the mobile Proton Mail app does not support fulltext search. I know why, but I still think it’s doable the same way as in the web browser. Anyway… that was a deal breaker to me. But now I already had Gmail + Gmail imported into Proton Mail + emails I received while already on Proton. I started to look for ways to go back to Gmail but also to take my Proton mail with me. I set up Thunderbird with IMAP and started to move them around. I didn’t finish that process because it was manual and there was just too much, I couldn’t keep track of it properly. I just created a mess for myself with doubled emails, etc. Sigh. I went back to Gmail for a few years.

Then as I started using Thunderbird more and more I realized its fulltext search works across all inboxes even if the provider doesn’t support it. I had the urge to give Proton another go. This time I was also already using SimpleLogin (before Proton bought them). I had a different personal domain. What I now created is that I have TWO inboxes (Gmail and Proton) and never moved fully away from Gmail. But I do use SimpleLogin for both. It was because I wasn’t sure if I could commit 100% to Proton, given my past experience.

At this stage, I was still using Bitwarden. So I had Bitwarden + Proton Mail + Gmail + SimpleLogin. But I knew of Proton Pass, which a couple years earlier was lacking compared to Bitwarden, but supposedly has improved. I decided to give it a try after Proton bought SimpleLogin, because it seemed like it would be cheaper to user Proton Mail + Proton Pass + SimpleLogin, I wouldn’t need Bitwarden anymore. I really like the UX of Proton Pass. The desktop app is pretty and functional. I love how 2FA codes in desktop web browsers are displayed automatically in a notification and I can use them by clicking a single button. Autofill on Android also works 90% of time. So I imported everything from Bitwarden into Proton Pass and decided to “test drive” for a bit. Part of the test was creating new logins in PP. At first I manually added them to Bitwarden. After some time, I didn’t. I created a bunch of passkeys in PP, also part of the functionality test. So they are now not in Bitwarden.

Meantime, I started to be bothered by some Proton things. Some login forms don’t autofill, for example a bank website that I use many times every month. I reported it to Proton on November 6 last year. They said they forwarded it to their team and that it will get fixed in the next release. It didn’t. It still does not work 5 months later. In the meantime I stumbled upon several other websites where Proton Pass’ autofill does not work. But at least Proton launched a few half-baked products since then. Fulltext search on Android doesn’t work, either. It’s been only 8 years or so, I can wait.

I also realized that I probably don’t need an encrypted inbox. It’s not even E2EE, because that’s simply impossible in email domain (unless it’s something like S/MIME or PGP, but both parties have to use it). It’s only encrypted on rest. I am no activist nor a journalist. I just add extra work for myself, having to run Proton Bridge, having to use their apps, not having a working fulltext search in the mobile app, not having normal IMAP.

I feel like them launching more and more apps and services is going the way of creating an “ecosystem”. I was happy having SL as an independent service, now it’s also Proton. I feel like an Apple customer (been there), I see the garden walls being built around me and have an encroaching feeling of vendor lock-in.

I regret my choices. I did fumble. I want to go back.

I’m thinking of subscribing for Mailbox.org. I looked at Tuta (have to use their apps, not easy to export), Posteo (doesn’t allow for custom domains) and FastMail (I had issues in 2018, don’t remember what exactly, besides I want an EU product). Because of how butchered my Proton inbox is, I think the best approach will be to delete all Gmail messages from it (after I confirm they are still in Gmail) and then export all and import to Mailbox.org. Separately, export all from Gmail and also import into Mailbox.org. That should give me a clean slate. I will also change ownership of aliases in SL. Sadly, I used many passmail.com aliases which are probably bound to Proton Mail and I am not sure I can continue using them if I pay for SL, but not for Proton (though, my subscription is still valid for many months).

I want to migrate back to Bitwarden. Based on my search it’s not possible to selectively import entries from Proton Pass to Bitwarden. Currently my Bitwarden vault is outdated, Proton Pass has many newer logins and other items and several passkeys. I think what I have to do is backup my Bitwarden vault (just in case) and then create a new empty vault and import everything from Proton Pass. I also need to re-create any PP passkeys in Bitwarden and either switch the websites to use that or add Bitwarden passkeys if a website supports more than one passkey.

I am also not sure about staying on SL. I am considering Addy, but it’s run by just one guy, so I’m not sure about it. This time, I plan to buy another personal domain and use it for email aliases rather than to rely on the domains provided by the service. This way I can migrate in the future if I need to.

btw I also switched from Windows 11 to Linux

The core issue here is that I couldn’t commit . I wanted to try things and instead of committing to one and sticking to it, I used both at the same time. Chaos.

I just need to get this off my chest. Thanks for reading. I appreciate if you have anything constructive to say.