Cannot send GPG signed mails after upgrade

p3k's Avatar


02 Aug, 2013 08:57 AM

Which of our tools is giving you problems?


What’s the version of that tool?


What version of OS X are you using?


Please describe your problem. Add as much detail as possible.

When I hit the send button of a message signed with my PGP key, the message window disappears and immediately re-appears; the message is not sent.

Please describe what you did expect instead

The message should be sent.

If you remember, please describe the steps leading up to the problem

Worked flawlessly before upgrade to 2.0.1.

  1. Support Staff 1 Posted by Luke Le on 02 Aug, 2013 09:04 AM

    Luke Le's Avatar


    very sorry to hear that.
    Could you please open and check if you see any error messages in regards to the following search terms:
    - gpg
    - gpgmail
    - pinentry


  2. 2 Posted by interface on 02 Aug, 2013 09:42 AM

    interface's Avatar

    hi luke

    thanks for the quick reply.

    i get the following in

    * hundreds of lines stating

    org.gpgtools.macgpg2.gpg-agent: gpg-agent[4188]: a gpg-agent is already running - not starting a new one (org.gpgtools.macgpg2.gpg-agent[4188]) Exited with code: 2 (org.gpgtools.macgpg2.gpg-agent) Throttling respawn: Will start in 10 seconds

    * three lines stating

    [0x0-0x1a05a04].org.gpgtools.gpgkeychainaccess: objc[6111]: Object 0x100225100 of class NSPathStore2 autoreleased with no pool in place - just leaking - break on objc_autoreleaseNoPool() to debug

    (i guess that was when i started

    * one line stating

    Mail: Loaded GPGMail 2.0.1

    * nothing for pinentry.

    please let me know what else you could need for debugging this issue.


    On 02.08.2013, at 11:04, Luke Le wrote:

  3. Support Staff 3 Posted by Luke Le on 02 Aug, 2013 10:10 AM

    Luke Le's Avatar

    Not the most comfortable way to solve issues, but could you try restarting
    your Mac unless you've already done that?

  4. 4 Posted by interface on 03 Aug, 2013 12:24 PM

    interface's Avatar

    unfortunately, the issue remains after restart.

    any more ideas?


    On 02.08.2013, at 12:10, Luke Le wrote:

  5. Support Staff 5 Posted by Luke Le on 04 Aug, 2013 01:00 AM

    Luke Le's Avatar


    i've just found out that in the case you can't be asked for your passphrase, because the program responsible for that, doesn't work as it should, you're not seeing any error.
    Already fixed this bug and in the next version, you'll at least see an appropriate error message, which will also help us debug these problems.

    Now let's fix this problem.
    Could you please post the contents of your gpg-agent.conf file.
    It's located in the .gnupg folder in your users folder.

  6. 6 Posted by Randolph on 04 Aug, 2013 02:36 AM

    Randolph's Avatar

    I'm seeing the same problem. The "pinentry-program" indeed references a file which does not exist.

    File attached.

  7. Support Staff 7 Posted by Luke Le on 04 Aug, 2013 02:38 AM

    Luke Le's Avatar

    Yes, exactly.
    Our installer should fix that, but as it seems, fails to do so at the moment.

    Please change the line to /usr/local/MacGPG2/libexec/

    After that everything should work as expected.

  8. 8 Posted by Randolph M. Fri... on 04 Aug, 2013 02:47 AM

    Randolph M. Fritz's Avatar

    After a "killall -1 gpg-agent", that indeed fixed the problem.


  9. 9 Posted by Randolph M.Frit... on 04 Aug, 2013 02:53 AM

    Randolph M.Fritz's Avatar

    Since you are being so helpful...

    Is there also supposed to be a new 64-bit "GnuPG" preferences pane? Or is that something to be removed? The one I have is version 1.2.2 from 2006, and I suspect it was supposed to be replaced by the new installer.


  10. Support Staff 10 Posted by Luke Le on 04 Aug, 2013 03:14 AM

    Luke Le's Avatar

    Yes there is, and it should have been installed and is called GPGPreferences.

    Should look like in the attached picture

  11. 11 Posted by Randolph M. Fri... on 04 Aug, 2013 03:18 AM

    Randolph M. Fritz's Avatar

    There is, but the earlier pane has not been removed. I'll take it out.

    The new prefs pane seems to have many fewer options. Is there an advanced mode? Or are all those options now buried in text files?


  12. 12 Posted by interface on 04 Aug, 2013 07:04 AM

    interface's Avatar

    thanks luke for your help.

    i now followed the advice meanwhile given in this thread and changed the setting in gpg-agent.conf – which made sending pgp signed messages working again!


    On 04.08.2013, at 03:00, Luke Le wrote:

  13. Support Staff 13 Posted by Steve on 04 Aug, 2013 01:05 PM

    Steve's Avatar

    We've tickets for this problems:

    Closing this discussion. It will be re-opened as soon as the ticket is closed so you'll receive a notification. Feel free to open a new discussions should you run into further problems or need assistance.

  14. Steve closed this discussion on 04 Aug, 2013 01:05 PM.

  15. Support Staff 14 Posted by Steve on 06 Aug, 2013 10:03 AM

    Steve's Avatar

    Hi Tobi,

    we have a new GPG Suite ready that should fix this problem.

    Please download then mount the .dmg file and run the Install.

    Let us know if things run smoothly with that version. Looking forward to your feedback.

    Best :)

  16. Support Staff 15 Posted by Steve on 17 Aug, 2013 04:07 PM

    Steve's Avatar

    Tobi, I'm closing this discussion. If you like to add anything you can always re-open.

  17. Steve closed this discussion on 17 Aug, 2013 04:07 PM.

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