Set-up can be daunting, but I always found that entering one's password every time a new mail comes in is unbearable. They should highlight that the pgp password timeout can be changed to something less intrusive.
_________
1: http://www.gnupg.org/related_software/frontends.html
3: http://support.gpgtools.org/kb/how-to/first-steps-where-do-i...
>When you run GPG Keychain Access for the first time, the window will be empty or contain only the GPGTools Project Key (delivered via the GPGTools Installer).
>If you don't have a private key, you'll be prompted to create a new key pair.
I don't use OSX, but can you comment on how easy key exchange is nowadays?
I have to admit that I have it set up and ready to roll, but pretty much no one I know is willing to take the plunge.
Maybe when at work, but at home most people (Especially of the older generation) seem to check their email a few times a day.
Corporate users should never be using webmail on their work computer...If they're MS Exchange based, they should be using Outlook and their exchange policy should allow (and prefer) S/MIME. There are a variety of plugins for Outlook that support GPG and S/MIME is already signed and encrypted.
Pubkey's should always be make available through the existing online PKI services. I personally send all my keys through pgp.mit.edu to be mirrored world-wide. Key-exchange (For High to Ultimate trust scenarios) is simple and easy. Send someone your pubkey by signing it with their pubkey and email it in a signed email (with signed attachments) to them. Have them do the reverse.