As a FreeBSD committer, I also run FreeBSD on a lot of my machines. I recently upgraded my desktop with portupgrade and found that gnupg no longer worked. I got the error message:
gpg-agent[13068]: can’t connect server: `ERR 67109133 can’t exec `/usr/local/bin/pinentry’: No such file or directory’
gpg-agent[13068]: can’t connect to the PIN entry module: IPC connect call failed
gpg-agent[13068]: 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.
rdist 
Salamo Alikom
this is help but i wonder why i get this msg when i gen new key :
can’t connect to `/home/$USER/.gnupg/S.gpg-agent’: No such file or directory
and this msg :
Warning: using insecure memory!
even i set permission as said in GnuPG faq ,do you have effective solution ?
man gpg-agent or Google both answer your question.
thanks. it’s now over three years since you wrote this, yet it remains the solution to a still existent quirk.