Enigmail, GPG2 and Homebrew message decrypt problem

28th March 2015 – 226 words

After a recent upgrade of Enigmail, the Thunderbird addon for GnuPG encryption, I received a warning that my installed GPG version of 1.4 is old and future versions of Enigmail will only support GPG2.

You are using GnuPG version 1.4.19.
This is the last version of Enigmail to support this version of GnuPG. Future version only work with GnuPG 2.0 and newer.
We therefore recommend that you upgrade to the latest version of GnuPG 2.0.x.

Because I am using Homebrew for installing tools, I just installed GPG2 via brew:

brew install gpg2

Unfortunately, after a restart of Thunderbird, the key management didn’t work anymore; when signing or decrypting a message, I got this error:

enigmail <0x123123> Key not found or not valid. The (sub-)key might have expired. gpg2

After some googling, I found this (Spanish) blog post:

Turns out, one has to install another tool, Pinentry-mac, and set the Pinentry-program to that tool:

brew install pinentry-mac

and edit this file:

$ vim .gnupg/gpg-agent.conf

pinentry-program /usr/local/bin/pinentry-mac
default-cache-ttl 1800

After pressing “reset” in Enigmail preferences window, I still got a warning about timeout settings, but message decryption worked again.

If it still not work, try running the Enigmail “Setup Wizard” again and select your old key.