gpg signing emails with outlook?

Does anybody know of a “sane” way of doing this with Outlook 2003?
I’ve been scouring the web for the last couple of weeks trying to find a sane solution and have hit a brick wall.
The plugins I have come across including this one simply won’t work, as they expect me to generate a key based on an email address, which I don’t want or need to do.
Getting it to work with Thunderbird and Enigmail on linux (ubuntu) or windows is easy.
Why does Outlook have to be so awkward?