Back in 2018, I mentioned that there was reliable way to enter a gpg password on the cygwin console: http://cygwin.1069669.n5.nabble.com/pinentry-curses-not-available-td143121.html From there I was able to cobble together a solution using a locally patched version of pinentry-curses. Somewhere along the line, that stopped working. I am now back where I started. Does anyone have a solution for the following: 1. ssh into a windows box running cygwin sshd 2. run `echo hello | gpg -sab` This worked until recently. Now I get: gpg: using "01D5A625A30C0E6A" as default secret key for signing gpg: signing failed: Invalid IPC response gpg: signing failed: Invalid IPC response checking the output of gpg-agent, I see: gpg-agent[2261]: gpg-agent (GnuPG) 2.2.13-unknown started gpg-agent[2261]: handler 0x200549e0 for fd 7 started gpg-agent[2261]: starting a new PIN Entry cbreak failure, exiting gpg-agent[2261]: failed to unprotect the secret key: Operation cancelled pinentry-w32 works, but it pops up a GUI window and thus requires an RDP session. Does anyone have a working solution that doesn't require access to the windows console? -- David Dombrowsky, Software Engineer davek@6thstreetradio.org | 518-374-3204 https://www.linkedin.com/in/david-dombrowsky-94334415