Since I have worked on something similar, in my opinion, it isn't the downloading software that is necessarily a hurdle (although I agree that it is a bit of one); it is around the general difficulty and pain around your local setup and finding the user you are trying to contact's pgp key. This has been discussed at length, but I think it comes down to pgp being enough of a hassle that people who aren't focused on privacy/security don't bother using it.
With ssh keys, at least we can assume that if someone has a github account they have a private ssh key, and it is accessible through the github api. With pgp there isn't a guarantee that they even have a pgp key, and accessibility is on the users themselves to publish it in some way. I think that keybase.io has tried to become the go-to spot for pgp keys, but the adoption is nowhere near what github has, and again, someone has to be interested in privacy/security to want to do this as well.
I mean with all do respect that you are correct in terms of a better protocol, and that there are tools that exist that already do this. The concern that I think OP and myself are interested in solving is creating something that is quick, easy, and piggie-backs on top of the huge github userbase and provides a base level of encryption.
I just don't buy it. Using Github-registered SSH keys to communicate is also an idiosyncratic and complicated way to exchange messages (evidence: far, far more people use PGP than use schemes like this). It's also much less secure.
function encrypt(public_key, file) {
var pem_pub_key = sshKeyToPEM(public_key); // convert rsa to pem
var chunks = [];
var buffer = new Buffer(fs.readFileSync(file, 'utf8'));
// work around for 214 character limit for encrypting
// text with small openssh rsa pub key
for (var i = 0; i <= (buffer.length / 214); i++) {
chunks.push(buffer.slice(i * 214, (i * 214) + 214));
}
chunks.forEach(function(chunk) {
var encrypted = crypto.publicEncrypt(pem_pub_key, new Buffer(chunk));
console.log(encrypted.toString('base64'));
});
}
According to the docs, crypto.publicEncrypt uses OAEP by default, so the bulk of the terribleness should mainly be how horribly slow this is. It does clearly indicate that the author has no idea what they're doing, though.
Edit: For some reason I thought OAEP included randomness. It does not, which should mean you can guess-and-check the plaintext.
It's awful crypto and it made me throw up in my mouth a little bit. They should be using RSA to encrypt a random key then encrypting the rest of the message with some sort of authenticated encryption.
Sorry I made you barf ryan-c. If you have any interest in making this better I'd be willing to convert your constructive criticism into code. Issues are open on GH :)
1. Tools to encrypt messages using Github SSH keys are probably not a good idea. They're no more usable than real message encryption solutions, but have far more constraints.
2. You cannot safely use RSA like a normal cipher. RSA is a tool for building crypto protocols. The way you've deployed it here has a serious vulnerability.
If you want to build things that use cryptography, I think you really need to work with a high-level library. Nacl (or libsodium) is a great example of a package that goes out of its way to bulletproof itself.
The point is that it's using ECB mode with RSA, which indicates the developer has no real knowledge of crypto and is just blindly using pairs of "encrypt/decrypt" functions from Node's built-in crypto lib (which is essentially a thing wrapper around OpenSSL and thus joins its illustrious legacy of encouraging developers to make catastrophic cryptographic implementation mistakes).
In encryptMessage.js, the plaintext is split into chunks, and then chunks.forEach encrypts each chunk (via crypto.publicEncrypt) independently, and concatenates the chunks to form the ciphertext, aka ECB mode. You shouldn't use ECB mode with any cipher because it is not semantically secure. This is Crypto 101.
In addition, it's a bit wacky to use RSA encryption on your entire message because RSA operations are slow and you are limited to encrypting messages that are the length of your RSA key (well, minus the padding, which is how this developer arrived at the "split plaintext into 214 byte chunks" workaround).
A better solution (in every way) would be to use a "hybrid" encryption scheme, similar to TLS or GPG. To do this, you would:
1. Generate a random key for use with a symmetric cipher (e.g. AES-256)
2. Encrypt the plaintext with the random key, using a secure block mode (e.g. CBC, CTR)
3. Encrypt the random key with the RSA public key
4. Package those things together and share it on Github
Efficient and secure. Also totally unnecessary (you basically just reinvented a subset of GPG) but that's neither here nor there.
I love this comment. Thank you for putting the time in to proposing a more thorough solution. I will take this (and other) comments into consideration, and make some much needed improvements :)
There are a whole bunch of things you're likely to get wrong trying to design your own "hybrid" encryption system. It's not easy. Why not spend some time learning how to break crypto before you start building it?
I agree. There are whole classes of problems that are not at all obvious until one has spent time learning how to break bad crypto. Matasano's challenges[0] (which I think tptacek helped create) are a good start.
It appears to be using Node's crypto library to apply the RSA transform directly to the plaintext in modulus-size chunks. The problem isn't the quality of the RSA implementation.
Cool, but what I love more about this (post) is how helpful the comments are!
It reminds me of the old bash.org quote that basically said the best way to get help from the Internet is not to ask, but to assert an answer, and let people correct you.
I have also built something similar, I knew of the existence of cipherhub, but my goal was to focus on the ease of use, with the browser (https://mailbeam.io and https://github.com/bobbywilson0/gh-message). I do admit that my solution is not as easy as it should be yet.
You should consider with RSA keys have a limited size message that can be encrypted (e.g. for 2048 bit keys you are limited to 256 bytes in your message). My solution was to use the SSH key to encrypt the secret I used to encrypt the message with.
This is great. Thanks for sharing! I could definitely see building out something similar on top of private-message once I firm up the scripts with a more secure block mode.
IIRC, asymmetric key encryption is not preferred for large message lengths -- maybe the author could consider embedding an randomly generated AES key, and using that to encrypt the message instead?
I ran into this issue, I couldn't encrypt really large strings so I chunked the plain text. Not sure why that is the case. I would consider doing something like what you suggest, though I'm not sure exactly how I'd implement it. If you're interested in showing me how, I'd love to collaborate on some code with you (start an issue! https://github.com/sadasystems/private-message/issues)
I ended up doing this for a project that I wanted to have use RSA for large chunks of data, for sending it was:
1. Generate random AES cipher key (I used a 16 byte key) using any available secure rng (it all depends on where the thing gets it's entropy, I think node's crypto.getRandomBytes is supposed to be strong)
2. Pad & Encrypt data with AES
3. Encrypt randomly-generated key with RSA
4. Send the message in an envelope like: {key: <RSA encrypted AES key>, data: <AES encrypted data>}
For me, the devil was in the details -- padding took an especially long time for me to understand and solve (the thing I was working on was cross platform, so ruby->js or python->ruby, and of course not all implementations pad the same way), but once that was solved, most other things were easy. The node part was also particularly troubling because I had to deal with the way to specify encodings in node, which was kind of confusing (I spent a lot of time messing with base64/binary encoding and having my terminal start showing gibberish when I tried to print binary data)
I don't have access to that code now (I actually wrote it in order to get around the fact that internal networks at a certain company I used to work at didn't have a custom rootCA/support TLS properly), otherwise I'd just post it.