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The state of secure, encrypted messaging

Everyone should have an expectation of being able to communicate with someone else in a verifiably secure manner. I have a particular fascination with secure communications and encryption and I’ve spent a lot of time thinking through my own pragmatic approach to secure messaging.

This is my write up of the current state of things as I’ve found it.

E-mail encryption & PGP #

E-mail seems to be considered a secure way to communicate but it is actually about as safe as sending a postcard in the mail, despite it being used for all sorts of private and confidential communications.

Progress has been made with major providers encrypting mail in transit, but once it reaches your inbox, the message is still open to the provider or anyone who might gain access to your mail account.

Sensitive files, personal information and discussions many would want to keep secret are stored in inboxes, often indefinitely. If you use a free email service, your emails are scanned for advertising.

The solution is encryption, and PGP is the standard. However, there are a multitude of problems that make PGP unworkable:

  • The security model itself relies on the security of the keys. If the keys become compromised, all past messages can be decrypted i.e. It has no forward secrecy.
  • Managing keys is a hassle — you have to very careful with your private key. Storing them in the cloud defeats the point and browser based encryption has concerns, so it has to be stored on your local system which can leave it vulnerable to malware or a permissions mistake. It is recommended to store keys on a hardware device such as a YubiKey but setting one up to handle PGP is not particularly easy.
  • There are no good mobile email clients which support PGP. There are several apps for iOS (which is the only secure mobile OS) but they are either outdated, have minimal functionality or require an odd workflow rather than being a fully featured mobile client. Further, you have to trust they are doing the right things with your keys. And if you follow best practice and use a YubiKey, you cannot plug that into a mobile device.
  • Encrypted email cannot be parsed by your mail server spam filters, apply intelligent filtering or for server side search. I actually think that Apple Mail on OS X has better search than GMail, but search on iOS isn’t as good and with the volume of emails I get, using something like Sanebox (which is what I use) or Priority Inbox simply wouldn’t work as well on encrypted messages.

As a result, it is very difficult to get non-technical users to adopt PGP and if you make use of it yourself, you lose a lot of necessary functionality for keeping your inbox manageable.

I did find an interesting approach used by a small number of mail providers whereby they will encrypt all incoming email with your public PGP key (after spam filtering) so all your messages are encrypted in storage. There are some challenges with this approach, such as being unable to easily encrypt your “Sent Mail” folder, which will of course contain the full email thread but you could simply disable remote storage of sent mail. And of course it only protects messages on your side – the recipient still has a plain text copy! seemed to be the most reputable of the few mail providers who offer this but you still face all the same problems above as if you had used PGP in the first place.

Given all the above limitations, with modern workflows and mobile access in particular (indeed, mobile accessis the most secure way to manage your email), using PGP is basically unworkable. A conclusion many others have come to.

iMessage & WhatsApp #

Probably the two most widely used, mobile-first messaging apps. WhatsApp is significantly further ahead because of its cross platform capabilities, but iMessage is also popular due to it being the iOS default.

For me, the most convenient aspect of iMessage is its support for all Apple platforms. You can seamlessly move between iPhone, iPad, Mac and Watch. Whenever I try a new messaging app, this is the biggest thing that always brings me back to iMessage.

It is also secure, but the key model means that you have to trust Apple. I believe that given Tim Cook’s public position on privacy and security — specifically stating that iMessage communication cannot be read — Apple has so much to lose in reputation by allowing access to the police/security services that they won’t risk it. As such, we can trust the service. This is sufficient for most people.

WhatsApp is owned by Facebook, a company I do not trust. However, the end to end encryption is implemented using the Signal protocol and backed by Moxie Marlinspike, who I do trust. The fact that so many people use WhatsApp and its group messaging functionality is also a major point in its favor. The recent Guardian reporting to the contrary is simply wrong, and highly damaging to the Guardian’s reputation for quality journalism.

The problem with both of these services is the metadata that is collected. Information about who you are communicating with and when can reveal a lot, and should be considered as sensitive as the content itself. They are also both operated by corporations who you may or may not trust to manage the keys for you and backups to the cloud are enabled by default, so it is trivial for them to access your communications without having to break into or backdoor the service itself.

Signal and Keybase #

These apps are both best in class when it comes to security. They are both open source and are highly regarded in the security community. Signal is the most mature and used by high profile potential targets. And in the case of Keybase, you control the keys.

The problem for casual users is convenience. Compared to WhatsApp and iMessage, they are not very popular and there is limited support for non-mobile platforms. Signal has a desktop client but it is not standalone and requires Chrome to be running. This makes for a sub-optimal UX, especially if you don’t use Chrome as your browser. The UI doesn’t really fit into the design guidelines of macOS and unless it is open and running, you won’t get notifications.

Keybase just recently released their iOS and Android app, but it is quite obvious it has been built using a non-native framework (React Native) with some lag and buginess (at least on iOS). It is still early and I am particularly interested in it for KBFS, which is the first client-encrypted cloud filesystem. Once that comes to the mobile app and the bugs resolved, then it will be a great alternative to iCloud Drive/Google Drive/Dropbox.

Other apps? #

The only generally accepted “secure” apps are those mentioned above. Apps like CryptoCat (dubious security history) and Telegram are not.

Wire looks interesting but I’ve not had an opportunity to test it.

Mobile apps only for casual use? #

For me, iMessage, WhatsApp, Signal and Keybase all suffer from the same problem of not being appropriate for long form communication. The mobile-first approach with a small screen means it is difficult to use them as a replacement for email, especially if you are dealing with attachments.

The rise of voice based computing and assistants like Google Home, Alexa and Siri will also be hampered by encrypting your messages. Users might like to be able to have their mail read to them, or to instruct the assistant to dictate a reply to messages. There’s obviously little point encrypting messages if you’ve already read them out to an assistant which uses cloud services to transcribe the audio!

And good luck trying to get your lawyer or accountant to communicate with you only using Signal or Keybase!

A pragmatic approach #

Users will ultimately use the services which: a) most people use; b) have the least friction. This means email, iMessage and WhatsApp. Those who really need security and/or are tech savvy will use Signal. Keybase looks promising, but there’s still a risk it will remain niche.

The big problem is that users don’t really seam to care about secure messaging. Most people simply don’t think about this often, and have a superficial view of why privacy is important, usually centering around the argument: “I have nothing to hide”. Most people also generally agree that the security services should have unfettered access to communication for investigatory purposes. That is a reasonable position but has more nuance because this is about broad, mass surveillance rather than targeted monitoring with judicial safeguards (which I have no problem with).

Given the inevitible use of email, iMessage and WhatsApp, there are some ways to mitigate risk:

  • Have an aggressive retention policy for deleting your files & emails. What doesn’t exist can’t be leaked! Only store the data you truly need or have a legal requirement to retain for a period of time.
  • Don’t use email as storage. Anything important and/or sensitive should be stored elsewhere, in an encrypted or otherwise secured form.
  • Use the retention options in your messaging app: expiring messages are supported by Signal and iMessage allows you to auto-delete your history after a period of time (but note this doesn’t apply to messages sync’d to macOS, which you must manually delete).
  • Disable SMS.
  • Consider email to be public. If you wouldn’t be happy saying it in public, then don’t send it via email.
  • Don’t send attachments. Upload files to cloud storage and share the link. Then you control whether the file remains shared or not, and precisely who can access it.
  • Use a second channel to verify any requests sent via email.

Finally, a good checklist of general security principles is worth reviewing.