Geeks on Coffee

UPDATE 3-Feb-2009: GPGMail for Leopard is out of beta and now includes a handy script for installing the bundle. You can use that in place of the sub-steps in Step 4.

I’ve been using encrypted email on Windows for a coupla years new, courtesy of Thunderbird and the wonderful Enigmail. Moving to the world of Mac, I’ve decided to migrate to Mail, rather than sticking to Tbird, so Enigmail’s not going to work in the new environment. To that end, I’m venturing forth to find a Mac-y counterpart, and have decided to chronicle that journey here.

A few disclaimers before we begin: I’m working on Leopard, so your mileage may vary. More importantly, I already have cryptographic keys that I’ll be moving over from my old system, so these instructions won’t include information about setting up your own keys, or even getting your keys ready for importing in the new system. I’m also assuming you can install software without too much hand holding. With that out of the way, let’s get started:

1. Get GNU Privacy Guard and GPG Keychain Access from http://macgpg.sourceforge.net/
   MacGPG is the OS X native version of the GNU Privacy Guard (GPG) software. It’s equivalent to Gpg4Win in that it takes the gpg package from *nix and makes it easily installable in places without direct access to the normal *nix install tools.
2. Install GNU Privacy Guard, followed by GPG Keychain Access
   There’s nothing special here. One’s an install package, and the other is the standard copy-to-the-Apps-folder thing.
3. Open GPG Keychain Access and import your private keys
   The first time you load Keychain Access, it will notice you don’t have keys and ask what you want to do about that. Click ‘Import’ and then find your keys. With any luck, your private key should now show up on the Secret tab, and any other keys should be displayed as appropriate.
4. Now, go get GPGMail from http://www.sente.ch/software/GPGMail/English.lproj/GPGMail.html and install it.
   Since I’m using Leopard, I’ll be using the beta version. Detailed installation instructions are included in the dmg, but can be summed up as:
   1. Quit Mail
   2. Copy GPGMail.mailbundle (from the file you downloaded) to the folder Library/Mail/Bundles/ in your home directory, creating folders as needed
   3. Execute the following in the Terminal:
      defaults write com.apple.mail EnableBundles -bool yes
      defaults write com.apple.mail BundleCompatibilityVersion -int 3
   4. Restart Mail

All other things being equal, your keys should now be ready to use in Mail, which is the goal. You can safely stop here, but I’m going to go one step further and add a bit of GPG integration to the Address Book.

1. Go get ABKey from http://abkey.far-blue.co.uk/
2. Install ABKey by copying ABKey.bundle to the /Library/Address Book Plug-Ins/ folder in your home directory

You should now be able to see the gpg keys of any contacts in your keychain right in Address Book.
And there ya go. One quick, easy transfer of secure email to the Mac. Hope you find it helpful.

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Address Book, GPG, Mail