I recently updated to latest gnupg and pinentry version via homebrew, which unfortunately broke my setup. I suddenly got this error when decrypting with gpg:

...
gpg: public key decryption failed: No pinentry
gpg: decryption failed: No pinentry
...

Looking into ~/.gnupg/gpg-agent.conf this first line showed:

pinentry-program /usr/local/bin/pinentry-mac

This is right and the same what which pinentry-mac returns. So why the error? I turns out ` /usr/local/bin/pinentry-mac` is a symbol link which (apparently?) the gpg-agent doesn’t follow. So trick was to set the final path, for me that’s:

pinentry-program /usr/local/Cellar/pinentry-mac/1.1.1.1/bin/pinentry-mac

And, BOOM! It works again.

Further sources:

• https://superuser.com/questions/1628782/gpg-signing-failed-no-pinentry

Original issue and comments

https://github.com/rngtng/rngtng.github.io/issues/16