[TriLUG] How do I create an encryption key for windows Outlook from a linux box

[Cristóbal Palmer]

On Fri, Jun 18, 2010 at 5:19 PM, Ralph Blach <chipperb at nc.rr.com> wrote:
> My sister uses Microsoft windows outlook for her mail client, and I cannot
> see here changing.
>
> How do I create a certificate, which I can send to here which she can import
> and I can encrypt
> mail against.

This isn't the answer to the question you asked, but it's the answer
to the question you (perhaps) should have asked, which is, "How can I
have private text conversations with my sister, who is on a Windows
machine?"

The answer is that you should help her install Pidgin and the OTR
plugin. Pidgin you're probably already familiar with, as it is the
default chat client for several distros, with the notable exception of
Ubuntu, which switched to Empathy a few releases back. I dislike
Empathy (the software) because it does not support OTR. What is OTR?
http://www.cypherpunks.ca/otr/ should cover that nicely. So the combo
of Pidgin and OTR is a winner for a variety of reasons, but will not
suit you if you're not comfortable with the jump from asynchronous
email to (mostly) synchronous IM. Some of the reasons I specifically
like it:

1. End-to-end encryption

With certificates or with SSL to the chat server, there is the
possibility that a third party could read the messages. While this is
fairly implausible, it is possible.

2. Set up once, use worry-free afterward

Once you've set up OTR and verified your interlocutor, you don't have
to worry about it again unless one of you has to reinstall pidgin, get
a new laptop, etc. No buttons to push when sending messages. Nothing
to remember to do. Email certificates and PGP, on the other hand....
I've seen otherwise intelligent people mess these up.

3. Platform agnostic. Chat network agnostic.

Yahoo? Google Talk? AIM? Windows? Mac? Linux? Doesn't matter. This
combo will work, with the caveat that for a Mac the person should be
using Adium, not Pidgin.

Cheers,
-- 
Cristóbal M. Palmer
ibiblio.org systems
UNC Chapel Hill