@werner I was hoping to make a modified gpg-agent build that would let me walk through what's going on after the nonce is sent but it looks like the gpg4win process only takes in a package of pre-built gpg binaries which rules that out. As far as I can figure out, after the nonce is read and accepted, libassuan creates a stream object out of the socket and then finding nothing in the stream terminates the ssh handler. We send the actual client request immediately after the nonce but in a separate call to send() so I now wonder if by not having anything read in at the same time as the nonce gpg-agent or libassuan thinks that it's a 0-length stream.

I just took a look through assuan-socket.c and it appears that we just need to send the nonce and don't need to read anything back. We also found a bug on our side that was preventing the nonce from being sent, which has been fixed. The error message logged above no longer happens.

@werner After sending the nonce value from the socket file, does anything need to be read back before ssh-agent commands can be sent? Are there any byte ordering requirements for sending the nonce or can they be sent in the same order as they are in the file?

I've been working with one of Microsoft's developers on a temporary tool that should bridge the connection between named pipes and the Unix sockets emulation used by gpg-agent but things appear to trip up with sending the nonce. From the position of the tool, the nonce value is successfully sent (send returns 16), but never seems to be picked up by gpg-agent. Instead both gpg-agent and the bridge sit there until whatever tool is using them (I test using ssh-add -l) is terminated, at which point gpg-agent immediately spits up the message

I would argue that the Windows port of OpenSSH is not unstable at this point, especially given that Microsoft is even providing it as an installable feature in the next regular Windows 10 release. The fact that the port is now using actual OpenSSH version numbers instead of their own 0.x versions lends credence to this as well.