S/MIME via remote Outlook (Citrix)

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given the following scenario:
4 employees are connected to a Windows 2000 Server via Citrix XenApp client.
They use Outlook 2003 to send/receive email, and have a S/MIME certificate
installed. The security level in Ooutlook is set to "high", and all used
passwords are strong.

I know that security on a foreign controlled system is something which
seems to be impossible, but I want to find out if the possible security
risks could possibly fit into the considered concept/model.

Is it possible for the server operator to get the passwords and/or the
cleartext of encrypted messages? How would this be done, in such case?

The connection between the clients and the server is encrypted. I'm quite
aware of the possibility that in case of a server crash, unencrypted
plaintext could get dumped onto the harddisk.

What else is practically possible?

Thanks a lot!

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