Since migrating to GnuPG 2.1 and gnome-keyring 3.18, I have lost the ability to
use password SAVED in the keyring.
The password prompt now appears every now and then. Even if I click "Save
password" checkbox in the pinentry prompt, I'll be asked for it again next time
when I log in.
This is a regression. Previously, I only had to type keyring password and it
would supply GnuPG with the PGP Key passphrase.
What distribution are you using? What pinentry program? Can you take a look
using seahorse to make sure that your password is saved. Once it is saved, it
shouldn't be removed.
This is Linux From Scratch, pinentry 0.9.7, pinentry -> pinentry-gtk-2, with
fallback to ncurses. No other pinentry program works.
This is KDE environment, Qt pinentry crashes. I can confirm that there's a
keyring password in the Login keyring, which is the only keyring I use.
Nonetheless, the password won't be asked again while the gpg-agent is running,
the password was entered at least once, and the "Remember password (or
whatever)" box was checked.
As soon as gpg-agent is terminated or a session restarted (which also terminates
gpg-agent), next time I try to use the pgp key, I get asked for its passphrase.
I just tested this with Fedora 26, pinentry-gnome3 0.9.7 and Gnome Keyring 3.20.1. See below for a full trace. If this doesn't work for you, check that you have compiled pinentry with libsecret, and did not deactivate the feature in the gpg-agent.conf.
$ pinentry-gnome3 OK Pleased to meet you OPTION allow-external-password-cache OK SETKEYINFO test OK GETPIN D 1234 OK $ pkill gpg-agent $ pinentry-gnome3 OK Pleased to meet you OPTION allow-external-password-cache OK SETKEYINFO test OK GETPIN S PASSWORD_FROM_CACHE D 1234 OK