I’m using my stationary PC for building packages, so most of the time I’m accessing this server via SSH. Almost everything is working fine, except pinentry (curses) which isn’t asking for a password during repository signing. Fortunately, reprepro has option that you can pass in command line which will force password question. The flag is --ask-passphrase and here’s an example command:

reprepro --ask-passphrase -b .. include unstable *.changes