"I sure would appreciate if someone could tell me if this is a bad idea and 
why, the more I know now at this time the better."

Encryption adds latency to your traffic, double encryption just adds another 
delay.  While this extra layer of security may be necessary for servers that 
have processing power to handle the load, one should weigh the pros and cons of 
client-to-server.  It is asking a lot for a laptop to do this and not have 
users notice the delay, even in today's dual-core machines.  Also important is 
that both ends of the SSH/SSL tunnel be under the same control, which is 
usually typical for IPSec site-to-site VPNs.  I do not notice the delay on my 
64-bit dual core desktop, when connecting to remote servers using 
double-encryption.  The quality of the connection is key; in my case I have a 
controlled environment going through the same provider (Sprint) between Los 
Angeles and London (i.e. I use IPSec tunnel mode for the site-to-site, then 
IPSec transport for server-to-server).  While IPSec is different in 
implementation than your SSL/SSH they essentially perform the same function of 
providing a secure tunnel through which to transmit/receive critical/private 
information.  Do you also have control over both ends of your connection?

I have always found that profit and productivity come before security.  If this 
setup is for secure monitoring or securing data between servers (for example) 
this may provide some additional piece of mind for your customer.  If this is 
for the CEO or VP of Sales/Marketing to securely connect to your LAN, this 
solution will have a short existence.

Good luck!

Edward Ray
(SecAdmin)

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