On Tue, Jul 02, 2013 at 03:18:54PM -0400, Rob Owens wrote:
> Icedove/Thunderbird has the Enigmail extension to handle encryption.  
> You might want to give that a try as well, particularly since you are
> trying to encourage others to use encryption and Thunderbird is available
> for both Linux and Windows (and Mac?).

Yes, I used to use Thunderbird/Enigmail, and it is what I recommend to
non-technical people, though I haven't used it recently myself (I
don't much like GUI mail clients).  Does Thunderbird/Enigmail have a
way to search through encrypted mail?  I don't remember this being
available last time I used it.

> In my experience, email encryption is has been pretty easy with the
> exception of getting it to work with webmail.

It's pretty easy to get up *sending and reading* encrypted mail, and
there are lots of guides out there about how to do that much.  But as
I'm learning now, some of the other features of mail that people rely
on become a lot harder or even impossible when their messages are
encrypted.  The big ones are searching, and accessing mail from a
machine you don't control (part of the webmail problem).

> The other tricky thing is getting people to understand the concepts
> of how/why to trust a key -- things like verifying the fingerprint,
> etc.

Mm, yes, I haven't even thought about that much myself.  I'm still
pretty much the only PGP user among people I communicate with
regularly, so I haven't come across anybody who is wondering whether
to trust my key.  Guess I'll cross that bridge when I come to it...

Thanks again for your input!

Best,
Richard



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