After the 2013 Snowden revelations, there has been a push to make email more private than it currently is (which is, essentially, like writing on a postcard). The big guns, Google and Yahoo, have wowed to make their respective email systems end-to-end (E2E) encrypted but progress has been slow. The official page about the Google effort has not been updated for months (as of June 2015). In this article, I go over some options available today, while we wait for that final solution that, at this pace, might still take a while to come.
Given that they all do the essential thing in some way or another, I looked into other desirable features of an end-to-end email system. Here’s a description of each feature:
- No need to change address. It’s a hassle if you need to use a different email address in order to have privacy. Here a Yes means that you can continue using your current email provider and address, and still obtain the benefit of encryption.
- Provider doesn’t store secrets. If it does, there’s always the danger that they’ll be forced to reveal them. Now, some providers store them in encrypted form, which is better, but still they’re storing something sensitive essentially forever.
- Provider cannot read email. As ludicrous as this may sound, at least one of the providers featured in this article is able to read your emails, or enable someone else to do so. We are assuming the encrypted content is easy to intercept.
- Account not required. Because some of us are paranoid enough to prefer not being forced to make an account anywhere, to prevent being tracked when we use it, or whatever other reason.
- Encrypt attachments. Not all we send is text. Often the sensitive information will be a picture, document, or any other kind of file. Encryption should be able to handle this.
- Encryption visible. A study published in 2013 showed that, for the time being, users prefer to see their messages in encrypted form at some point, in order to be assured that they are indeed encrypted before they send them out. They were willing to go as far as cutting and pasting the material in order to get this. This feature does not need to be on 100% of the time, but at least as an option.
- Encryption can be disguised. A number of users need encryption because they fear they are under surveillance. They would be even happier if they could make their emails and attachments appear as if they were not encrypted at all. This is called steganography, and at least one of the systems reviewed adds this feature to the mix.
- Forward secrecy. This means that the encrypted content remains secure into the future, even if the encryption key or the user password is obtained by an enemy. This is considered essential for instant messaging apps, and would be nice if email could also pull this trick, perhaps as an option.
- Multi-platform. It is no good if users need to use a particular kind of device (PC, iPhone, whatever) in this fractioned market.
- Portable across machines. This means that a give user should be able to use his/her E2E encrypted email on different machines, possibly of different kinds, with a minimum of risk and hassle.
- Multiple identities. What if several family members or coworkers share a computer? Can they keep privacy from each other? What if you’re schizophrenic or have multiple personalities?
- Open source. A deal-breaker for many, if it is not. Some of us feel a lot more reassured if the underlying code is available and experts can subject it to scrutiny.
- Crypto engine. There are a number of cryptographic engines out there, some more recent than others, but all the systems presented here use an engine that has accumulated at least ten years of scrutiny.
So here’s the comparison as a table. Yes is good, No is bad. Some entries have a footnote right below the table.
|Features||Enlocked 2||Virtru||Proton mail||Mailvelope||PassLok|
|No need to change address||Yes1||Yes1||No||Yes1||Yes|
|Provider doesn’t store secrets||No2||No||No2||Yes||Yes|
|Provider cannot read email||Yes||No||Yes||Yes||Yes|
|Account not required||No||No||No||Yes||Yes|
|Encryption can be disguised||No||No||No||No||Yes|
|Portable across machines||Yes6||Yes6||Yes||No||Yes|
|Overall score (# of yes)||5||4||5||6||12|
1. The app works only with certain email providers, not all of them
2. They do store encrypted private keys, hence the bad score
3. Separate encryption and delivery from server
4. They deny access to the encryption key (paid feature), but the key is not deleted
5. Browser plugins plus apps in iOS/Android stores
6. User secret data saved in servers (encrypted) enables this
Now a short description of each E2E provider, and why they got these scores.
Their first version got slammed by reviewers because it was doing the encryption on a server instead of the client. This meant that their server got to see the plain text of your private stuff, even though they promised (who doesn’t?) that they didn’t store it. Enlocked 2 is a browser plugin (standalone mobile apps exist) that performs PGP encryption on the client. Their server holds each user’s public key so it can be sent to other users who want to encrypt messages for the owners of those keys to read. The plugin automatically retrieves each public key belonging to a recipient in an email and uses it to encrypt the content before sending the encrypted result to the actual email provider. Because it is a plugin, it only works with Gmail, Yahoo mail, Outlook, and a handful more.
In order to achieve portability, Enlocked also stores and serves the user’s private key, previously encrypted by his/her password. This is a problem, since compromising that password or choosing a bad one (Enlocked accepts bad passwords without complaint) makes all your encrypted emails readable by Enlocked or those to whom they give your private key.
Enlocked is a commercial service, which costs $9.99 every month for sending 100 messages, and goes up from there. You can sign up for a free account, though, which allows you to decrypt an unlimited number of messages and encrypt 10 messages every month. Their system seems to be glitchy: I’ve tried for several days to make a free account without success, leading only to error screens that instruct me to contact support (without any link to support, though).
On the surface, Virtru behaves very much like Enlocked. They have slick plugins and mobile apps. They encrypt text and attachments. You only need your account password to use it anywhere you go. The difference is that they use symmetric encryption (256-bit AES) instead of asymmetric encryption (PGP). When you encrypt something, you send the actual, per message encryption key to Virtru, and they store it so they can give it to the recipients of your encrypted message. The whole process is quite automatic and makes it possible for new users to be added in a flash, since no initial key generation and exchange process is needed.
The downside is that they can read your encrypted messages, if intercepted (they are sent through your regular provider, from a limited list of supported ones), and enable anyone who asks nicely to do so. This should be a deal breaker for anyone who has real confidential material to protect. To make matters more egregious, they charge for “forward secrecy”, meaning that Virtru promises to no longer give the decryption key to anyone except you (and, possibly, government agencies).
If you don’t want the paid features, Virtru is free to use, though making an account is a must. A Pro account with the extra features will normally set you back $4 a month.
Proton Mail is Enlocked with an email server thrown in. When you sign up for Proton Mail, you sign up for the whole thing, and you get a firstname.lastname@example.org email address. No way to keep using your old address except by forwarding. Proton Mail requires the user to memorize two keys: one is for logging into the email server and getting your emails, plus obtaining the PGP public keys of other users automatically; the other is for encrypting your PGP private key, which is stored in their server so you can use different machines. Since they must know your login key in order to give you access, they’d also be able to read your encrypted mails if both keys were the same, hence the need for two separate keys.
Proton mail is accessed strictly as a website, so no plugins or mobile apps are involved. Interestingly, this approach makes it accessible from any device, running any operating system.
Proton Mail just finished beta and is available for signups, everything is free, though not open source. I believe that Google’s and Yahoo’s E2E solutions, when they come, will end up looking a lot like Proton Mail.
If Proton Mail was Enlocked plus a mail server, Mailvelope is Enlocked minus a key server. It uses PGP like the other two, but key generation is kept strictly to your machine. The user is responsible for distributing his/her public key to others, and for safeguarding his/her private key, which is locally stored encrypted by a password. Mailvelope is only available as a Chrome extension and off the box it is limited to Gmail, Yahoo mail and a couple more, though apparently you can configure other clients manually (I didn’t try). Integration with those is quite slick, however, as Mailvelope detects encrypted incoming emails and offers to decrypt them if only you supply the password.
This extension may be all that many people will ever need, so long as they don’t use encrypted email with a lot of people (public key entry and selection is a bit involved) and don’t need portability (settings don’t sync across machines).
Obviously it was a foregone conclusion that PassLok was going to be the winner in a comparison made by its own developer. I won’t dispute that, but the fact remains that PassLok has all the desirable features on the list. You can use it with your existing email (in fact, with any program at all). It doesn’t store your content or even anything secret. It doesn’t talk to servers so you’re not making any account anywhere. It handles files as well as text. It runs as a Chrome plugin, iOS/Android app, or just as a webpage that gets completely cached so you don’t even need an Internet connection after the first time. It includes a full complement of text and image steganography tools so your encrypted material can slip undetected. In its Chrome app incarnation, it even syncs all your stored public keys (which are not secret, but may be hard to obtain again) using Google’s servers. It is possibly the only web app available today capable of making a self-destructing message, where the key needed to decrypt it disappears from the face of the earth as soon as it is read once.
But it must have some defects, right? C’mon!
A lot of PassLok’s security lies in the fact that it is self-contained code, and precisely this is why some things are harder to do than in other systems. PassLok does not interact with email clients, and so the user must manually copy and paste the encrypted material between PassLok and whatever email client you are using. This is a hassle, but it has the advantage that you know without a doubt that your data is encrypted before it gets to your email. Some email providers, like Google, log every keystroke you type into the compose window, so it is important to encrypt your messages before the email program sees them.
PassLok does run a server to help users obtain other users’ public keys. It is called General Directory, and currently it is manual rather than automatic so that the main PassLok code is isolated from contact with any server. A lot of things in PassLok are automatic, but nothing is forced on the user. If the user decides not to make public his public key, but rather send it to a selected few, that’s okay with PassLok. Most PassLok users actually do this. They are a paranoid but dedicated bunch.