where to start?

[Robert J. Hansen]

Dr. Scott S. Jones wrote:
> I run both Win xp and ubuntu 8.10. My wife runs win xp on her laptop. We are
> at the point now where we both want to enable encrypted emailing AND we want
> to find a nice way of educating those we email to often, or with whom we
> exchange sensitive information, in how to use gnupg to encrypt email back
> and forth. Where should I start? 

You've already done it.  :)  Welcome to the community!  You'll find
we're a pretty friendly bunch here.

I would start by asking whether you want things to "just work" or
whether you want to take a more direct hand in things.  The former
will... well... just work.  The latter will require a lot more work, but
I personally find it more rewarding.

That choice is the first fork in the road.

If you want to go down "just work," the best thing for you to do is use
S/MIME, the Secure Multipurpose Internet Mail Extensions.  If you want
to go down "learn a lot and have control," then I would suggest OpenPGP.

GnuPG supports both S/MIME and OpenPGP, so both are on-topic for this
mailing list.  Let us know what you want, and we'll be in a much better
position to offer you help.  :)