Post Syndicated from original https://mjg59.dreamwidth.org/65874.html

Github accidentally committed their SSH RSA private key to a repository, and now a bunch of people’s infrastructure is broken because it needs to be updated to trust the new key. This is obviously bad, but what’s frustrating is that there’s no inherent need for it to be – almost all the technological components needed to both reduce the initial risk and to make the transition seamless already exist.

But first, let’s talk about what actually happened here. You’re probably used to the idea of TLS certificates from using browsers. Every website that supports TLS has an asymmetric pair of keys divided into a public key and a private key. When you contact the website, it gives you a certificate that contains the public key, and your browser then performs a series of cryptographic operations against it to (a) verify that the remote site possesses the private key (which prevents someone just copying the certificate to another system and pretending to be the legitimate site), and (b) generate an ephemeral encryption key that’s used to actually encrypt the traffic between your browser and the site. But what stops an attacker from simply giving you a fake certificate that contains their public key? The certificate is itself signed by a certificate authority (CA), and your browser is configured to trust a preconfigured set of CAs. CAs will not give someone a signed certificate unless they prove they have legitimate ownership of the site in question, so (in theory) an attacker will never be able to obtain a fake certificate for a legitimate site.

This infrastructure is used for pretty much every protocol that can use TLS, including things like SMTP and IMAP. But SSH doesn’t use TLS, and doesn’t participate in any of this infrastructure. Instead, SSH tends to take a “Trust on First Use” (TOFU) model – the first time you ssh into a server, you receive a prompt asking you whether you trust its public key, and then you probably hit the “Yes” button and get on with your life. This works fine up until the point where the key changes, and SSH suddenly starts complaining that there’s a mismatch and something awful could be happening (like someone intercepting your traffic and directing it to their own server with their own keys). Users are then supposed to verify whether this change is legitimate, and if so remove the old keys and add the new ones. This is tedious and risks users just saying “Yes” again, and if it happens too often an attacker can simply redirect target users to their own server and through sheer fatigue at dealing with this crap the user will probably trust the malicious server.

Why not certificates? OpenSSH actually does support certificates, but not in the way you might expect. There’s a custom format that’s significantly less complicated than the X509 certificate format used in TLS. Basically, an SSH certificate just contains a public key, a list of hostnames it’s good for, and a signature from a CA. There’s no pre-existing set of trusted CAs, so anyone could generate a certificate that claims it’s valid for, say, github.com. This isn’t really a problem, though, because right now nothing pays attention to SSH host certificates unless there’s some manual configuration.

(It’s actually possible to glue the general PKI infrastructure into SSH certificates. Please do not do this)

So let’s look at what happened in the Github case. The first question is “How could the private key have been somewhere that could be committed to a repository in the first place?”. I have no unique insight into what happened at Github, so this is conjecture, but I’m reasonably confident in it. Github deals with a large number of transactions per second. Github.com is not a single computer – it’s a large number of machines. All of those need to have access to the same private key, because otherwise git would complain that the private key had changed whenever it connected to a machine with a different private key (the alternative would be to use a different IP address for every frontend server, but that would instead force users to repeatedly accept additional keys every time they connect to a new IP address). Something needs to be responsible for deploying that private key to new systems as they’re brought up, which means there’s ample opportunity for it to accidentally end up in the wrong place.

Now, best practices suggest that this should be avoided by simply placing the private key in a hardware module that performs the cryptographic operations, ensuring that nobody can ever get at the private key. The problem faced here is that HSMs typically aren’t going to be fast enough to handle the number of requests per second that Github deals with. This can be avoided by using something like a Nitro Enclave, but you’re still going to need a bunch of these in different geographic locales because otherwise your front ends are still going to be limited by the need to talk to an enclave on the other side of the planet, and now you’re still having to deal with distributing the private key to a bunch of systems.

What if we could have the best of both worlds – the performance of private keys that just happily live on the servers, and the security of private keys that live in HSMs? Unsurprisingly, we can! The SSH private key could be deployed to every front end server, but every minute it could call out to an HSM-backed service and request a new SSH host certificate signed by a private key in the HSM. If clients are configured to trust the key that’s signing the certificates, then it doesn’t matter what the private key on the servers is – the client will see that there’s a valid certificate and will trust the key, even if it changes. Restricting the validity of the certificate to a small window of time means that if a key is compromised an attacker can’t do much with it – the moment you become aware of that you stop signing new certificates, and once all the existing ones expire the old private key becomes useless. You roll out a new private key with new certificates signed by the same CA and clients just carry on trusting it without any manual involvement.

Why don’t we have this already? The main problem is that client tooling just doesn’t handle this well. OpenSSH has no way to do TOFU for CAs, just the keys themselves. This means there’s no way to do a git clone ssh://[email protected]/whatever and get a prompt asking you to trust Github’s CA. Instead, you need to add a @cert-authority github.com (key) line to your known_hosts file by hand, and since approximately nobody’s going to do that there’s only marginal benefit in going to the effort to implement this infrastructure. The most important thing we can do to improve the security of the SSH ecosystem is to make it easier to use certificates, and that means improving the behaviour of the clients.

It should be noted that certificates aren’t the only approach to handling key migration. OpenSSH supports a protocol for key rotation, basically by allowing the server to provide a set of multiple trusted keys that the client can cache, and then invalidating old ones. Unfortunately this still requires that the “new” private keys be deployed in the same way as the old ones, so any screwup that results in one private key being leaked may well also result in the additional keys being leaked. I prefer the certificate approach.

Finally, I’ve seen a couple of people imply that the blame here should be attached to whoever or whatever caused the private key to be committed to a repository in the first place. This is a terrible take. Humans will make mistakes, and your systems should be resilient against that. There’s no individual at fault here – there’s a series of design decisions that made it possible for a bad outcome to occur, and in a better universe they wouldn’t have been necessary. Let’s work on building that better universe.

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