Trying to shake off GMail

I’ve been recently more and more interested in switching from GMail to other more privacy-minded service which would not be willing to sell my data or track me. After researching for different options I’ve found three which I think stood out.

Updated post (14/04/2018)

Updates: this post has been updated with new information.

Motivation

After recent events (i.e. the whole Facebook thing, where I didn’t have an account, btw. and finding myself on haveibeenpwnd), my urge to stop depending on using Google services for everything became stronger. In particular, I became more aware of what am I selling when I’m accepting Google’s services for free: my data.

Thus, what I am looking for currently is another e-mail service which can ultimately replace google’s, which at least promises not to track me or sell my data and, even better, cannot actually have it since it is encrypted.

Specifically, to me, this means I want a service where my e-mails will only be stored encrypted on the server. Also, I would like to be able to use my PGP key (well, maybe one day Keybase’s keyring) if I want to send a signed message or encrypt it. Now, I don’t really expect to receive encrypted e-mail from someone (at least not often) nor I think someone would be willing to deal with encrypted messages if I sent them. However, signing a message can be really useful. Furthermore, I understand and expect that this service will be paid (although should not be expensive) since otherwise I cannot expect them to uphold their contract of not tracking me or selling my data.

In any case, I don’t actually deal with particularly sensitive data so I’m not specially worried about sending or receiving unencrypted e-mails. In my case I mostly care about safe-guarding my data from greedy companies and from possible data breaches.

So, after looking a lot for options, I found mostly three which I will describe in terms of what I look for. I’m excluding others which did not met the basic needs I described (for example, they explicitly say the do not support OpenPGP, are too expensive or do not offer any trial).

ProtonMail

This one was the first that I tried. This is probably the number one recommendation on many sites, probably because it is the most popular (I guess appearing on Mr. Robot series didn’t hurt).

After registering for a free plan here’s what I’ve found:

Updated 14/04/18:

MailFence

After trying ProtonMail for a while and seeing how they chose to implement encryption (ie. behind the curtains), I looked around for another compatible service which did not require you to upload your private key (but still encrypt incoming mail with your public key). I then also registered for a free account. Here are my findings:

Update (14/04/2018):

Mailbox.org

So, at this point I could either choose to have my inbox completely encrypted but being forced to give away my (passphrase encrypted) private key or accept not having my e-mails encrypted at all.

Luckily, I’ve found a promising one (although still not a clear choice) which is mailbox.org. What I can say is:

So, which one?

Right know I’m still waiting for ProtonMail to announce OpenPGP support to see how it would compare to mailbox.org. On one hand I like to have the inbox to be searchable, which is only possible if the decrypt for you with your key (which I don’t like so much). On the other hand, mailbox.org is quite cheaper (no message limits!) and allows you to handle your own key.

Furthermore, with mailbox.org I don’t think I would ever use their web interface since it sucks, so I would only use Thunderbird and maybe K-9 on Android. With ProtonMail I can at least use the web interface if I want but I’m also interested in how does the bridge work and if OpenPGP support will mean that I can have more control over the key or not.

So, I guess I will know in a few months.

Appendix: PGP capable e-mail clients (Linux and Android)

While playing with mailbox.org and testing how would I use it via e-mail clients, I tried Thunderbird+Enigmail on Linux and K-9+OpenKeyChain on Android.

In general I can say that both have to be closely configured to ensure that you actually achieve what you want. In my case, I don’t want to leave unencrypted e-mail in the server. This means that Drafts and Sent e-mail copies should not be stored in clear-text when sending unencrypted e-mails.

Enigmail can be configure to save encrypted Drafts but requires a strange workaround to save encrypted copies of Sent e-mails. What I did was to add a filter that would save an encrypted copy of the e-mail in the Sent folder, after being sent. I’m not entirely sure if this means that it will be saved in clear-text first and then encrypted, which would not be advisable if it were a service such as Google. Another (ridiculous) option which is sometimes recommended is to disable saving the clear-text copy of the e-mail and bcc:‘ing yourself every e-mail which would come back encrypted (if your server encrypts incoming e-mail).

Besides these small (but important) issues, my other gripe is with Thunderbird itself. I come from a past of using Thunderbird, then switching to Sylpheed and then Claws since it was so memory-heavy. Also, it looks a bit dated and I grown accustomed to GMail’s conversation style of browsing e-mails (damn you Google!). While there are other clients, none are actually better, prettier or GPG capable, IMHO.

On the Android side, I intalled K-9 since I already read so much about it and I like the OpenKeyChain app which allows using SmartCards. In this case the problem was that it simply did not save encrypted drafts of e-mails which are not yet marked as being encrypted. Let alone saving encrypted copies of non-encrypted Sent e-mails. UPDATE: as you can see in the issue comments, encrypted drafts will be an option soon. Maybe Sent e-mails can be encrypted later as well.

So… this means that suddenly something like ProtonMail seems more attractive. But yet, handing over your key is quite convenient until sometime someone manages to key-log your passphrase3.

With some-luck, I’ll have a clear decision soon.


  1. ProtonMail maintains OpenPGP.js, which means it will probably be based on that [return]
  2. Supposeddly there’s a way to access a discount which was active during Black Friday but I haven’t verified it yet [return]
  3. Why-oh-why doesn’t anyone else allows encrypting these keys with another PGP key which only you have, a-la Keybase? [return]
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