Unable to sign messages with GPG Mail plug-in (v. 2.5, build 1009)

Pertinax77's Avatar


12 Aug, 2015 03:21 PM

I recently upgraded to the latest version of the GPG Suite (2015.06). But I've noticed that there appears to be a problem with signing with my private key using Apple Mail and the GPG Mail plug-in. I get the following error (screenshot also attached):

The PIN-Entry helper responsible for asking for your passphrase seems to be defect.
To fix this problem, re-install the newest version of GPGTools
Should your problem persist, please contact us at https://gpgtools.tenderapp.com/ with the following error description:
gpg: problem with the agent: No pinentry
gpg: skipped "16ECD8E4ED64045FC6A00C6802069D787F5E05F7": Operation cancelled
gpg: signing failed: Operation cancelled
  1. 1 Posted by Bonelator on 13 Aug, 2015 07:18 AM

    Bonelator's Avatar

    I've got the same problem.

    gpg: problem with the agent: No pinentry
    gpg: skipped "F7664B7B2C06EFBB8DD4FF938C3E1A3F48954C88": Operation cancelled
    gpg: signing failed: Operation cancelled
  2. Support Staff 2 Posted by Steve on 13 Aug, 2015 09:53 AM

    Steve's Avatar

    Hey Pertinax and Bonelater,

    this is a bug that we've been trying to squash for quite some time. The good news is, we finally were able to find a fix. The fix is currently in our nightly GPG Suite and will be included in the next stable release. Could you please download and install our latest nightly build and see if the problem persists. That page also has sig and SHA1 to verify the download.

    All the best, steve

    Disclaimer: This is a development version which has not been thoroughly tested yet - bugs or crashes are to be expected. Thanks for helping us test.

  3. 3 Posted by Pertinax77 on 13 Aug, 2015 06:39 PM

    Pertinax77's Avatar

    OK thanks, will try it out.

  4. 4 Posted by Pertinax77 on 13 Aug, 2015 07:02 PM

    Pertinax77's Avatar

    I've just installed it. It seems to sign messages now without any problems, but will keep any eye out for it.

    This is more of GnuPG question but what's the GnuPG command for generating the signature that I am seeing attached to outgoing messages for the key associated with my email?

  5. 5 Posted by Bonelator on 14 Aug, 2015 07:34 AM

    Bonelator's Avatar

    My error is also gone, so it seems to work.

  6. Support Staff 6 Posted by Steve on 14 Aug, 2015 02:52 PM

    Steve's Avatar

    Thank you both for your feedback!

    Closing and if you encounter any further issues, please open a new discussion anytime.


  7. Steve closed this discussion on 14 Aug, 2015 02:52 PM.

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