full-disclosure - SMTP Encryption (S/MIME) for Outlook question

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Message-ID: <20040331112048.06e4064a.volker.tanger@detewe.de>
From: volker.tanger at detewe.de (Volker Tanger)
Subject: SMTP Encryption (S/MIME) for Outlook question

Greetings!

On Tue, 30 Mar 2004 17:39:59 -0800 "Crist J. Clark"
<cristjc@...cast.net> wrote:
> Most email clients are pretty easy to use with respect to
> S/MIME... Once you get the certificates installed. PKI. Managing
> certificates for a decent-sized luser base is not fun.

And from our experience S/MIME standards are just standard within the
same product family. Outlook's S/MIME and Netscape's S/MIME won't work
together the last time we tried. 

> > What do other Win/Exchange/Outlook IT admins use for S/MIME?  

GnuPG (OpenPGP standard) ?

> > BTW, if there's something that will run on top of the SMTP gateway
> > server or the internal Exchange server to encrypt the message before
> > being routed to the Internet, this is also acceptable. 

A number of gateway servers. There is (was?) a software package from the
GnuPG group. There is the T/Bone gateway (at freshmeat - and from
http://www.bonelabs.com/). Utimaco has a crypto-gateway, too. 

Usually you'll want a single company-wide key when using a gateway to
ensure confidential mail across the internet. This way you'll have
plaintext emails via LAN though - if not using TLS.

Bye

Volker Tanger
ITK Security