Mail stuck on sending email

Mike J's Avatar

Mike J

05 Jul, 2018 06:26 AM

Which of our tools is giving you problems? I'm running PGP Suite on Mac OS.

Attach a screenshot of the version info for all installed components (how to: https://gpgtools.tenderapp.com/kb/faq/where-can-i-find-version-info...):

Describe your problem. Add as much detail as possible. I'm trying to send a signed email but Apple Mail is blocked on sending mail.

What did you expect instead The email to go through.

Describe steps leading to the problem. I was asked for the password to my key. I supplied it and hit send.

Are you using any other Mail.app plugins? No.

  1. Support Staff 1 Posted by Steve on 05 Jul, 2018 06:28 AM

    Steve's Avatar

    Hi Mike,

    welcome to the GPGTools support platform. Sorry you are having problems using GPG Suite.

    Are you seeing any error at all? If so, please attach a screenshot.

    Can you open TextEdit and encrypt and decrypt some sample text using your own key. Does that work?

    The following two Knowledge Base articles explain how GPGServices is used:

    • KB explaining how to encrypt and sign text or files
    • KB explaining decryption and verification

    Best,
    steve

  2. 2 Posted by Mike J on 06 Jul, 2018 05:02 AM

    Mike J's Avatar

    Hi Steve,

    Thanks for your answer. Encrypting from Finder times out. I get an error saying code 62.

  3. Support Staff 3 Posted by Steve on 06 Jul, 2018 11:44 AM

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    Can you restart your mac please. Does the problem persist then? If yes, please send a screenshot of the error message.

    Let's test gpg encryption and decryption in the terminal.

    1. click spotlight at the top right menubar and type 'terminal'
    2. open Terminal.app by pressing enter
    3. in the new terminal window
    4. paste the following without the ' 'gpg2 -ae --default-recipient-self <<<OK'
    5. a PGP message will be created
    6. paste the following without the ' 'gpg2 -ae --default-recipient-self <<<OK | gpg2 -d'
    7. you will be asked for your password (if your password is still in the cache or stored in macOS keychain you will not be asked)
    8. when everything is fine you should see the word "OK" in your terminal - in that case decryption worked as expected
  4. 4 Posted by Mike J on 08 Jul, 2018 06:30 PM

    Mike J's Avatar

    I get the following error:
    gpg: public key decryption failed: Timeout
    gpg: decryption failed: No secret key
    This is after gpg2 says the encryption is performed with the right key.

  5. Support Staff 5 Posted by Luke Le on 09 Jul, 2018 05:39 PM

    Luke Le's Avatar

    Hi Mike,

    is it in any way possible that you are using a custom gpg from homebrew/MacPorts/fink? These versions sometimes interfere with ours.

  6. 6 Posted by Mike J on 10 Jul, 2018 05:15 AM

    Mike J's Avatar

    No, I downloaded mine from gpgtools.org.

  7. 7 Posted by Mike J on 11 Jul, 2018 05:20 AM

    Mike J's Avatar

    So any other ideas? To sum up, the key is there for encrypting, but not for decrypting. gpg2 --list-secret-keys does show my private key.

  8. Support Staff 8 Posted by Steve on 11 Jul, 2018 10:45 AM

    Steve's Avatar

    Could you please send a debug log from your affected machine: Open System Preferences > GPG Suite > Send Report. Check the box to "attach debug log". Since you already described your issue in this discussion, you don't need to add a lot of detail, but please do add the link to your existing discussion, so I can then merge your debug info with this existing discussion.

    All the best,
    steve

  9. Steve closed this discussion on 20 Sep, 2018 04:24 PM.

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