(Disclaimer: I'm not a cryptographer, and I do not claim to be an expert in Signal. I've had this read over by a couple of people who are so with luck there's no egregious errors, but any mistakes here are mine)
There are
indications that Twitter is working on end-to-end encrypted DMs, likely building on work that was
done back in 2018. This made use of
libsignal, the reference implementation of the protocol used by the
Signal encrypted messaging app. There seems to be a fairly widespread perception that, since libsignal is widely deployed (it's also the basis for
WhatsApp's e2e encryption) and open source and has been worked on by a whole bunch of cryptography experts, choosing to use libsignal means that 90% of the work has already been done. And in some ways this is true - the security of the protocol is probably just fine. But there's rather more to producing a secure and usable client than just sprinkling on some libsignal.
(Aside: To be clear, I have no reason to believe that the people who were working on this feature in 2018 were unaware of this.
This thread kind of implies that the practical problems are why it didn't ship at the time. Given the reduction in Twitter's engineering headcount, and given the new leadership's espousal of political and social perspectives that don't line up terribly well with the bulk of the cryptography community, I have doubts that any implementation deployed in the near future will get all of these details right)
I was musing about this last night and someone pointed out
some prior art.
Bridgefy is a messaging app that uses Bluetooth as its transport layer, allowing messaging even in the absence of data services. The initial implementation involved a bunch of
custom cryptography, enabling a range of attacks ranging from denial of service to extracting plaintext from encrypted messages. In response to criticism Bridgefy replaced their custom cryptographic protocol with libsignal, but
that didn't fix everything. One issue is the potential for MITMing - keys are shared on first communication, but the client provided no mechanism to verify those keys, so a hostile actor could pretend to be a user, receive messages intended for that user, and then reencrypt them with the user's actual key. This isn't a weakness in libsignal, in the same way that the ability to add a custom certificate authority to a browser's trust store isn't a weakness in TLS. In Signal the app key distribution is all handled via Signal's servers, so if you're just using libsignal you need to implement the equivalent yourself.
The other issue was more subtle. libsignal has no awareness at all of the Bluetooth transport layer. Deciding where to send a message is up to the client, and these routing messages were spoofable. Any phone in the mesh could say "Send messages for Bob here", and other phones would do so. This should have been a denial of service at worst, since the messages for Bob would still be encrypted with Bob's key, so the attacker would be able to prevent Bob from receiving the messages but wouldn't be able to decrypt them. However, the code to decide where to send the message and the code to decide which key to encrypt the message with were separate, and the routing decision was made before the encryption key decision. An attacker could send a message saying "Route messages for Bob to me", and then another saying "Actually lol no I'm Mallory". If a message was sent between those two messages, the message intended for Bob would be delivered to Mallory's phone and encrypted with Mallory's key.
Again, this isn't a libsignal issue. libsignal encrypted the message using the key bundle it was told to encrypt it with, but the client code gave it a key bundle corresponding to the wrong user. A race condition in the client logic allowed messages intended for one person to be delivered to and readable by another.
This isn't the only case where client code has used libsignal poorly. The
Bond Touch is a Bluetooth-connected bracelet that you wear. Tapping it or drawing gestures sends a signal to your phone, which culminates in a message being sent to someone else's phone which sends a signal to their bracelet, which then vibrates and glows in order to indicate a specific sentiment. The idea is that you can send brief indications of your feelings to someone you care about by simply tapping on your wrist, and they can know what you're thinking without having to interrupt whatever they're doing at the time. It's kind of sweet in a way that I'm not, but it also advertised
"Private Spaces", a supposedly secure way to send chat messages and pictures, and that seemed more interesting. I grabbed the app and disassembled it, and found it was using libsignal. So I bought one and played with it, including dumping the traffic from the app. One important thing to realise is that libsignal is just the protocol library - it doesn't implement a server, and so you still need some way to get information between clients. And one of the bits of information you have to get between clients is the public key material.
Back when I played with this earlier this year, key distribution was implemented by uploading the public key to a database. The other end would download the public key, and everything works out fine. And this doesn't sound like a problem, given that the entire point of a public key is to be, well, public. Except that there was no access control on this database, and the filenames were simply phone numbers, so you could overwrite anyone's public key with one of your choosing. This didn't let you cause messages intended for them to be delivered to you, so exploiting this for anything other than a DoS would require another vulnerability somewhere, but there are contrived situations where this would potentially allow the privacy expectations to be broken.
Another issue with this app was its handling of one-time prekeys. When you send someone new a message via Signal, it's encrypted with a key derived from not only the recipient's identity key, but also from what's referred to as a "one-time prekey". Users generate a bunch of keypairs and upload the public half to the server. When you want to send a message to someone, you ask the server for one of their one-time prekeys and use that. Decrypting this message requires using the private half of the one-time prekey, and the recipient deletes it afterwards. This means that an attacker who intercepts a bunch of encrypted messages over the network and then later somehow obtains the long-term keys still won't be able to decrypt the messages, since they depended on keys that no longer exist. Since these one-time prekeys are only supposed to be used once (it's in the name!) there's a risk that they can all be consumed before they're replenished.
The spec regarding pre-keys says that servers should consider rate-limiting this, but the protocol also supports falling back to just not using one-time prekeys if they're exhausted (you lose the forward secrecy benefits, but it's still end-to-end encrypted). This implementation not only implemented no rate-limiting, making it easy to exhaust the one-time prekeys, it then also failed to fall back to running without them. Another easy way to force DoS.
(And, remember, a successful DoS on an encrypted communications channel potentially results in the users falling back to an unencrypted communications channel instead. DoS may not break the encrypted protocol, but it may be sufficient to obtain plaintext anyway)
And finally, there's
ClearSignal. I looked at this
earlier this year - it's avoided many of these pitfalls by literally just being a modified version of the official Signal client and using the existing Signal servers (it's even interoperable with Actual Signal), but it's then got a bunch of other weirdness. The Signal database (I /think/ including the keys, but I haven't completely verified that) gets backed up to an AWS S3 bucket, identified using something derived from a key using
KERI, and I've seen no external review of that whatsoever. So, who knows. It also has crash reporting enabled, and it's unclear how much internal state it sends on crashes, and it's also based on an extremely old version of Signal with the "You need to upgrade Signal" functionality disabled.
Three clients all using libsignal in one form or another, and three clients that do things wrong in ways that potentially have a privacy impact. Again, none of these issues are down to issues with libsignal, they're all in the code that surrounds it. And remember that Twitter probably has to worry about other issues as well! If I lose my phone I'm probably not going to worry too much about whether the messages sent through my weird bracelet app being gone forever, but losing all my Twitter DMs would be a significant change in behaviour from the status quo. But that's not an easy thing to do when you're not supposed to have access to any keys! Group chats? That's another significant problem to deal with. And making the messages readable through the web UI as well as on mobile means dealing with another set of key distribution issues. Get any of this wrong in one way and the user experience doesn't line up with expectations, get it wrong in another way and the worst case involves some of your users in countries with poor human rights records being executed.
Simply building something on top of libsignal doesn't mean it's secure. If you want meaningful functionality you need to build a lot of infrastructure around libsignal, and doing that well involves not just competent development and UX design, but also a strong understanding of security and cryptography. Given Twitter's lost most of their engineering and is led by someone who's alienated all the cryptographers I know, I wouldn't be optimistic.
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