tl;dr - pinentry (in particular pinentry-gnome3) stopped working, pinentry-emacs didn’t work well with daemon mode, just use pinentry-gtk or pinentry-qt5. This post outlines a shallow dive into a rabbit hole for a broken pinentry setup w/ Emacs – if your setup is already working, skip this. What is pinentry? When a program like Gnu Privacy Guard (AKA GnuPG, gpg) requires user input, but that entry has to be secure (and possibly access system password stores/keychains), how do they do it?