Two months ago I upgraded to PGP Desktop 9, because the new version would finally work with Eudora on Mac OS X. Indeed, all I had to do was install the new version, reboot, and the new automatic mode began immediately discovering and auto-enabling my email accounts as I used them. It does this with some clever connection redirection using the built-in Mac OS X firewall, courtesy of the Unix subsystem.

Unfortunately, the automatic mode doesn’t work so well if you are also using some kind of network tunnel, such as a VPN or ssh port forwarding, which is increasingly common for me as I take the laptop to clients or on the road.

I finally got around to figuring out how to set up PGP Messaging’s manual proxy mode, courtesy of decent instructions for Windows users written by Robert Johansen of PGP. I thought I would document the configuration for Mac OS X users, since there are substantial differences in the application between the two platforms.

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