Matthew Garrett

After my previous efforts, I wrote up a PKCS#11 module of my own that had no odd restrictions about using non-RSA keys and I tested it. And things looked much better - ssh successfully obtained the key, negotiated with the server to determine that it was present in authorized_keys, and then went to actually do the key verification step. At which point things went wrong - the Sign() method in my PKCS#11 module was never called, and a strange
debug1: identity_sign: sshkey_sign: error in libcrypto
sign_and_send_pubkey: signing failed for ECDSA "testkey": error in libcrypto"
error appeared in the ssh output. Odd. libcrypto was originally part of OpenSSL, but Apple ship the LibreSSL fork. Apple don't include the LibreSSL source in their public source repo, but do include OpenSSH. I grabbed the OpenSSH source and jumped through a whole bunch of hoops to make it build (it uses the macosx.internal SDK, which isn't publicly available, so I had to cobble together a bunch of headers from various places), and also installed upstream LibreSSL with a version number matching what Apple shipped. And everything worked - I logged into the server using a hardware-backed key.

Was the difference in OpenSSH or in LibreSSL? Telling my OpenSSH to use the system libcrypto resulted in the same failure, so it seemed pretty clear this was an issue with the Apple version of the library. The way all this works is that when OpenSSH has a challenge to sign, it calls ECDSA_do_sign(). This then calls ECDSA_do_sign_ex(), which in turn follows a function pointer to the actual signature method. By default this is a software implementation that expects to have the private key available, but you can also register your own callback that will be used instead. The OpenSSH PKCS#11 code does this by calling EC_KEY_set_method(), and as a result calling ECDSA_do_sign() ends up calling back into the PKCS#11 code that then calls into the module that communicates with the hardware and everything works.

Except it doesn't under macOS. Running under a debugger and setting a breakpoint on EC_do_sign(), I saw that we went down a code path with a function called ECDSA_do_sign_new(). This doesn't appear in any of the public source code, so seems to be an Apple-specific patch. I pushed Apple's libcrypto into Ghidra and looked at ECDSA_do_sign() and found something that approximates this:

nid = EC_GROUP_get_curve_name(curve);
if (nid == NID_X9_62_prime256v1) {
  return ECDSA_do_sign_new(dgst,dgst_len,eckey);
}
return ECDSA_do_sign_ex(dgst,dgst_len,NULL,NULL,eckey);

What this means is that if you ask ECDSA_do_sign() to sign something on a Mac, and if the key in question corresponds to the NIST P256 elliptic curve type, it goes down the ECDSA_do_sign_new() path and never calls the registered callback. This is the only key type supported by the Apple Secure Enclave, so I assume it's special-cased to do something with that. Unfortunately the consequence is that it's impossible to use a PKCS#11 module that uses Secure Enclave keys with the shipped version of OpenSSH under macOS. For now I'm working around this with an SSH agent built using Go's agent module, forwarding most requests through to the default session agent but appending hardware-backed keys and implementing signing with them, which is probably what I should have done in the first place.