You could use something like WinPT on the Windows systems to assist with signing and encryption. I believe that there are also a couple O/OE plugins for this. I've got a few listed on
my site, but it's been a while since I've tested them. If using O/OE is not a requirement, you could use a client that better supports GPG/PGP. The difficulty you'll find is key management. There are several decent key servers available.