There’s a new GPGMail app – installed with GPGTools – that works on Lion:
Unless you’ve got S/MIME set up. If you do have S/MIME set up, the bundle won’t display the settings, nor will it “work”. You’ll have a GPGMail preferences pane in, but the only options you get are enabling OpenPGP under Composing and Reading. You’re supposed to have the choice of keys, etc.

The previous GPGMail (a *long* time ago), allowed both S/MIME and OpenPGP, so this is a bit disappointing. Their bug tracker has that functionality scheduled for (possibly) version 2.1, and I’ll be trying it again at that point.

There are definitely challenges to having S/MIME and OpenPGP running the same mail client. If you (accidentally) try to do both at the same time, you get garbage that most mail clients can’t understand – because each mail client/plugin applies the encryption in a different order, and the recipient’s mail client would have to know that order. Now, if a person only has a PGP key or only has an S/MIME certificate, then it’s not that difficult – the mail client should select the appropriate encryption.

It is very nice to see that GPGMail is being developed actively again.

2 thoughts on “GPG on Lion – only if you don’t use S/MIME

  1. Mike Myers says:

    I was hoping this release would fix the annoying gpg-agent bug in which my private key passphrase would not store in the Keychain even though I checked that box every time. But it looks like the new release just throws out gpg-agent entirely (?). On the upside, at least now I can have OpenGPG cache the passphrase for a period of minutes. On the downside however, I shouldn’t have to, because this is exactly what Keychain is for.

    I guess I shouldn’t complain since at least it is being maintained like you said, but I wish the community could make PGP work half as seamlessly as S/MIME does. Nobody seems willing to pay a CA for an S/MIME cert; perhaps I can’t blame them.

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