Updated expired key to no longer expired... still can't encrypt emails

Justin Clift's Avatar

Justin Clift

04 Aug, 2015 12:28 PM

Went to send a GPG2 encrypted email (Apple Mail with GPGMail 2.5 (1009)), then realised my keypair expired a few months ago.

So, updated the keypair using GPG Keychain version 1.2 (1103), then sent the updated key to the public keyserver (right click on keypair in list → "Send public key to Keyserver". No errors so far.

Apple Mail is still not giving the option to encrypt email though. The lock icon is still greyed out, and hovering over it shows the tooltip of "This message can't be encrypted. You have to enter at least one recipient first." Which is bizarre, as there absolutely is the correct recipient, and the recipient has a valid GPG key (matching the exact email address) which can be seen using GPG Keychain.

Is this a known bug or something new or does anyone have suggestions? :)

  1. Support Staff 1 Posted by Steve on 06 Aug, 2015 11:09 AM

    Steve's Avatar

    Hi Justin,

    thanks for taking the time to report this problem. Could you please restart your mac, then double check your key is ok in GPG Keychain in the key details. Also check the sub key.

    Are you then able to send an encrypted and signed test mail to yourself with mail.app?

    All the best,

  2. 2 Posted by Justin Clift on 23 Aug, 2015 10:01 PM

    Justin Clift's Avatar

    Sorry for the delay Steve, just remembered this problem. :/

    Just looked at this, and the subkey was still the old date/expired. Just created a new one, exported to the keyserver (without issue), and the icon for encrypting emails is now available to use (didn't need to reboot in this instance). So, I think I'm good. :)

    As a thought, when a person changes the validity date of their key (to make an expired one valid), it might be useful to prompt them to create a new subkey too. Could help for people with less than a perfect understanding of GPG, to get them where they want. :)

    Thanks for your assistance Steve. :)

  3. Support Staff 3 Posted by Steve on 24 Aug, 2015 09:54 AM

    Steve's Avatar

    Absolutely agree. We should even inform the user prior to an expiring key or subkey.

    We have a ticket for this problem. I connected this discussion with the existing ticket. That means, should this discussion get closed, it will be re-opened as soon as the ticket is closed. That way you'll receive a notification. Feel free to open a new discussions should you run into further problems or need assistance.

    Glad, this is solved for you. I'm closing this discussion. If you need further assistance or have questions you can re-open this discussion here or open a new one any time.

    Best, steve

  4. Steve closed this discussion on 24 Aug, 2015 09:54 AM.

  5. Steve closed this discussion on 27 Aug, 2018 12:30 PM.

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