gpg on M$

[Anonymous Sender]

> i don't want them to be bothered by cutting-n-pasting... they'll be
> receiving PGP stuff, but probably not sending it. when a PGP email comes
> in, i'd like to have a little box come up and ask them for their secret
> pass-phrase, and then they can read the message in outlook...

I have read about a light mail proxy that does on the fly pgp
encryption (and decryption) before (resp. after) sending (receiving) the
message to (from) the real SMTP (POP3) server. I don't remember
whether it runs on windows, but if it does it could solve your problem
nicely. I don't remember the application name either, but it should
be on freshmeat.net.

Your client must configure the proxy (keys, trust, real servers etc) and
then tell her e-mail program to connect to localhost instead of the
real remote servers.