On 23/11/2016 13:44, Tao Bror Bojlén wrote:
Could it be that your GPG passphrase is saved in the macOS keychain?
That would explain why you aren't prompted for it after a reboot.

Try opening the macOS keychain and seeing if anything comes up when you
search for "gnupg".

I second that explanation.

I had to debug something similar for someone else, but in this case their ssh passphrase was being stored in the keychain after an upgrade to macOS 10.12. However it wasn't visible in keychain access. It needed to be removed manually using a sqlite command:

http://apple.stackexchange.com/questions/253779/macos-10-12-sierra-will-not-forget-my-ssh-keyfile-passphrase

The same might also be true with gpg passphrases and 10.12.

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