Issues with encrypting in

Mat's Avatar


19 Dec, 2011 12:12 AM

Hey guys -

I've gone through all of the threads regarding this issue but can't seem to get working. Any help would be greatly appreciated.

After upgrading to Lion, I was no longer able to decrypt in mail (it would spin with the "Loading..." message but never decrypt) and I couldn't encrypt (greyed out lock). Based on some of your other suggestions, I downloaded the new bundle ( and installed it. That fixed the decrypting problem beautifully but not the encrypting one.

I can use the services menu fine and encrypt inside a text file, but it doesn't seem to recognize the email addresses as known keys. What can I do to troubleshoot?

Thanks for all your work.

  1. 1 Posted by Alex on 19 Dec, 2011 05:56 PM

    Alex's Avatar

    You can only encrypt to e-mailaddresses you have the valid public keys for. Is it possible for you to send an encrypted mail to
    gpgtools-org (at)

  2. 2 Posted by Mat Henley on 19 Dec, 2011 06:01 PM

    Mat Henley's Avatar

    Hey Alex, thanks for the reply. Yeah, I'm a long time user and understand
    the fundamentals - the keys are all there, it's simply broken after I

    Here's a screenshot

  3. Support Staff 3 Posted by Luke Le on 19 Dec, 2011 06:05 PM

    Luke Le's Avatar

    Hi Mat,

    please verify that your Preferences -> GPGMail says
    Composing -> Enable OpenPGP/MIME

    I can see from your screenshot that it wants to use S/MIME.

    At the moment you have to change this setting before using S/MIME or OpenPGP.
    The upcoming version will let you switch from the composing window.

    Hope that helps

  4. 4 Posted by Alex on 19 Dec, 2011 06:06 PM

    Alex's Avatar

    Interesting. Good screenshot. What happens if you try to encrypt a file via command line?

    1. Open
    2. cd, enter
    3. echo test > testfile.txt, enter
    4. gpg -ae testfile.txt, enter
    5. gpgtools-org, enter
    6. enter
    7. gpg testfile.txt.asc
  5. 5 Posted by Alex on 19 Dec, 2011 06:07 PM

    Alex's Avatar

    @Lukas: yeah, you're right. S/MIME is being used...

  6. 6 Posted by Mat Henley on 19 Dec, 2011 06:36 PM

    Mat Henley's Avatar

    That did it! Thanks a ton guys.

  7. Alex closed this discussion on 19 Dec, 2011 06:44 PM.

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