I had some trouble after upgrading GPGTools to version 2020.2 on macOS Big Sur, where it would ignore my Yubikey smart card and I couldn’t unlock my stuff.
Every time I tried to use gpg (Yubikey inserted), I would get this error:
gpg: decryption failed: No secret key
This sent me into a wild rage, and after spending far too much time trying to debug with no results, I switched tactics; remove GPGTools and install gpg myself. While it’s still early days, and I am by no means a gpg expert (who is?), everything seems to be working fine.
Here’s how I did it.
Uninstall GPGTools ¶
I downloaded the uninstaller from the GPGTools website; that’s right, it is not included in the standard GPGTools installation. Another reason to ditch it.
Install GPG ¶
I used homebrew to install the required packages.
brew install gpg pinentry-mac # pinentry-mac is needed for smart cards.
I also added the two packages to my Brewfile .
diff --git a/Brewfile b/Brewfile index 683e138..9b0d988 100644 --- a/Brewfile +++ b/Brewfile @@ -13,6 +13,7 @@ brew "fzy" brew "git" brew "git-delta" brew "git-standup" +brew "gpg" brew "hugo" brew "imagemagick" brew "isync" @@ -27,6 +28,7 @@ brew "pandoc" brew "par" brew "pass" brew "pianobar" +brew "pinentry-mac" brew "rename" brew "ripgrep" brew "rust"
Configure GPG ¶
The gpg installation added a
.gnupg/ configuration directory to my
home folder. After some research, I added a few lines to
# ~/.gnupg/gpg.conf ask-cert-level use-agent auto-key-retrieve no-emit-version default-key D81A4957BAF06BCA6E060EE5461C015E032EF9CB # use your key # ~/.gnupg/gpg-agent.conf pinentry-program /usr/local/bin/pinentry-mac default-cache-ttl 600 max-cache-ttl 7200 debug-level basic log-file $HOME/.gnupg/gpg-agent.log # helpful for debugging
I was making progress, but when I tried to use gpg I would get this error:
gpg: OpenPGP card not available: No SmartCard daemon
This one took some time to figure out. I checked
my homebrew installation, and scdaemon existed at
I eventually figured out I needed a scdaemon configuration file, and I needed to pass in the name of my smart card there.
macOS comes with a command line tool for testing smart cards (PC/SC), which I used to get the machine name of my smart card.
I inserted my Yubikey and ran
pcsctest, which gave me this output:
MUSCLE PC/SC Lite Test Program Testing SCardEstablishContext : Command successful. Testing SCardGetStatusChange Please insert a working reader : Command successful. Testing SCardListReaders : Command successful. Reader 01: Yubico YubiKey OTP+FIDO+CCID Enter the reader number :
The “Reader” line is what we’re interested in. I copied the name of my
smart card, killed
pcsctest with a Ctrl-c, and pasted to a
# ~/.gnupg/scdaemon.conf reader-port "Yubico YubiKey OTP+FIDO+CCID"
Finishing up ¶
I had to restart gpg agent before my changed would take effect.
killall gpg-agent gpg-agent --daemon --homedir $HOME/.gnupg
And that’s it, things are working for me again, and I got to replace a large dependency (GPGTools) with a slightly smaller one (GPG).
Other resources ¶
Some links I found helpful in my journey to figuring this out.