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VPN: SSH or PGP



I have been reading VPN-HOWTO, in order to implement a VPN system at my
place. The two key technologies used here are Encryption of the VPN Tunnel
using SSH and PPP modification for pty redirection. I am yet to clearly
grasp the whole HOWTO.

I have a few questions with regard to SSH:

I read elsewhere that SSH is just one of the technologies use for
Encryption, which use a Public-Private Key pair. PGP, I am told, is a newer
and better technology. I have a Linux Server which is my Proxy to the
Internet and I have a Win2K server on my internal LAN, on to which I wish to
have VPN sessions. I also want to have a Digital Signature Server (CA), on
my internal LAN.

In this scenario, do I have to have a SSH server on the Proxy for VPN
system, and also have a PGP system on an internal Linux server for digital
signatures -- Too much -- Can't I have one encryption system which can
handle both VPN and CA? If I have a PGP on the proxy, then, can I use
slogin, sftp, stelnet and scp commands?? Moreover, with SSH, it seems I
can't use the keypairs in Outlook/Outlook Express??

Kindly enlighten!!

Anand