I've had an ongoing saga of trying to get gpg2's pinentry to work on the console, via an SSH session, without requiring a console window. I just tried rebuilding and testing from the latest git repo, and I still receive the same error: $ echo test | gpg -sab gpg: using "01D5A625A30C0E6A" as default secret key for signing gpg: signing failed: Operation cancelled gpg: signing failed: Operation cancelled The "Operation cancelled" comes from some command it's sending to the tty and that's failing. I haven't looked into it more than that. It isn't a system limitation, as `ssh-add` can prompt for a password all day. As an admittedly insecure work-around, I've forked the code and added something that will read the password from a file in the home directory. This is obviously sub-optimal, but it works. Since I sign every git commit and I'm the only user of this machine, it's a reasonable risk to take to allow me to conveniently sign my commits. The fork is here, in case anyone cares: https://github.com/ddombrowsky/pinentry/commits/secretfile If anyone has any opinions as to the real root cause, I'd be willing to look into it more. -- David Dombrowsky | Chief Software Engineer 6th Street Radio LLC | 6thstreetradio.org | 518-374-3204 https://www.linkedin.com/in/david-dombrowsky-94334415 V2VkIEF1ZyAgNSAwMjoxMzowMiBFRFQgMjAyMAo=