The Thunderbird-with-PGP experience on Windows is atrocious, absolutely disgraceful.
Here's what I blogged after trying it a few months ago:
I suspect the way most people on Windows will use PGP is by downloading GPG4Win and Enigmail. The fact that this is two separate things to install is a showstopper for a lot of people. Installation of Engimail requires right clicking on a link to save it, then locating the file in Windows Explorer and dragging it into an open Thunderbird window. I can do that and you can do that, but it's arcane wizardry for a significant portion of the population.
Also, the GPG installer appears to randomly crash under certain circumstances on Windows 8.
That's just installation. Then you have to get people to generate a key using a password that's different from the one they use to login to their email server. I suspect most users would have a difficult time using the GPG interface; it's very reminiscent of desktop Linux applications a decade ago.
Here's what I blogged after trying it a few months ago:
I suspect the way most people on Windows will use PGP is by downloading GPG4Win and Enigmail. The fact that this is two separate things to install is a showstopper for a lot of people. Installation of Engimail requires right clicking on a link to save it, then locating the file in Windows Explorer and dragging it into an open Thunderbird window. I can do that and you can do that, but it's arcane wizardry for a significant portion of the population.
Also, the GPG installer appears to randomly crash under certain circumstances on Windows 8.
That's just installation. Then you have to get people to generate a key using a password that's different from the one they use to login to their email server. I suspect most users would have a difficult time using the GPG interface; it's very reminiscent of desktop Linux applications a decade ago.
There's more, but it's too long for here: http://jamesgecko.com/everyone-should-use-pgp-but-its-kinda-...