Mac Mail Plugin not working with gpg-agent (2.2.17 < 2.2.18) when running homebrew gnupg in parallel

Will Coleman's Avatar

Will Coleman

02 Dec, 2019 06:51 PM

Which of our tools is giving you problems?
2019.2 Mail-plug-in for Mac,
Running PGPSuite 2019.2
Mac Homebrew:
- hopenpgp-tools
- gnupg
- pinentry-mac

I recently updated gnupg to 2.2.18, however, it appears that my system is defaulting to the older version of the gpg-agent (2.2.17). When running gpg --card-status, I get the following header:

gpg: WARNING: server 'gpg-agent' is older than us (2.2.17 < 2.2.18)
gpg: Note: Outdated servers may lack important security fixes.
gpg: Note: Use the command "gpgconf --kill all" to restart them.
gpg: WARNING: server 'scdaemon' is older than us (2.2.17 < 2.2.18)
gpg: Note: Outdated servers may lack important security fixes.
gpg: Note: Use the command "gpgconf --kill all" to restart them.

When I go and run gpgconf --kill-all and restart, gpg restarts and all is on 2.2.18, but my native Mac mail plugin no longer works (multiple restarts of mail and multiple re-plugs of my nano YubiKey). It throws a "Inappropriate ioctl for device" error in Mac Mail. If I run gpgconf --kill-all again, it reverts back to 2.2.17 and works. Is there something I'm missing here?

!! see attached screenshot for exact error. !!

  • Do I need to change a conf setting somewhere to get this all up to date?
  • why do I have a mismarch in scdeamon and gpg-agent all of a sudden?
  • the Mac mail plugin will only work when the server is running 2.2.17 and NOT 2.2.18.
  • I've restarted my Mac as well and it still retains the old version of gpg-agent and scdaemon, meaning, it works, but I can't get the newer versions of gpg-agent to start properly and as noted above, when they do run, the Mac Mail plug in for signing no longer works.

I have paid support for my Mac Mail client.

  1. 1 Posted by Will on 04 Dec, 2019 03:48 PM

    Will's Avatar

    Any update on this? I do pay for support and to wait 3 days for some response is somewhat dumb. What am I paying for exactly?

  2. Support Staff 2 Posted by Luke Le on 04 Dec, 2019 04:01 PM

    Luke Le's Avatar

    Hi Will,

    we are currently being swamped with support requests so please allow some more time than usual.

    It is currently not supported to use home-brew's GnuPG alongside ours.
    It's possible to get it to work, but more often than not it does not.

    Is there a particular reason why you currently need the newest version of GnuPG? If not, please uninstall homebrew's.

  3. 3 Posted by Will on 04 Dec, 2019 04:06 PM

    Will's Avatar

    nope, that works.. I didn't realize you didn't need gnupg? I removed it and the error disappeared. Do I need hopenpgp-tools? or pinentry-mac as well?

  4. Support Staff 4 Posted by Luke Le on 04 Dec, 2019 04:07 PM

    Luke Le's Avatar

    Not from homebrew. GPG Suite comes with everything you need regarding GnuPG.

  5. 5 Posted by Will on 04 Dec, 2019 04:09 PM

    Will's Avatar

    great, you can close this.

  6. Support Staff 6 Posted by Luke Le on 04 Dec, 2019 04:10 PM

    Luke Le's Avatar

    Perfect, glad it is working now.

  7. Luke Le closed this discussion on 04 Dec, 2019 04:10 PM.

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