gpg-agent: can’t connect server: `ERR 67109133 can’t exec `/usr/local/bin/pinentry’: No such file or directory’
gpg-agent: can’t connect to the PIN entry module: IPC connect call failed
gpg-agent: command get_passphrase failed: No pinentry
gpg: problem with the agent: No pinentry
I found these two articles and noticed that my gpg had been upgraded from the 1.x to 2.x series. The 1.x gpg had an integrated password entry prompt but 2.x requires an external package. This can be fixed by installing the security/pinentry port. I’m not sure why it wasn’t marked as a dependency for gpg2.