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CHALLENGE: LAN -> TRANSPARENT PROXY -> MULTIPLE VPNS. How to put it together?

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Hello all,

This is a question combining squid with firewall rule manipulation
(both  need to get along well...).

I have a LAN and a GATEWAY BOX that serves as a NAT for all of the
users behind the LAN.
MY goal is to make the box filter all http requests and once they are
clean route the traffic through a VPN.
Up to here everthing is easy if I have only one VPN.

The Challenge:


.The box that acts as the NAT gateway and PROXY has 10 different VPNs.

The BOX NATs a LAN of 20 users.

I need to be able to NAT a specific user to a specific VPN however
before that is done the http requests of that user should be filtered
by the proxy in the SAME box.


Example:
LanUser1 makes an http request -> The HTTP request is processed on a
BOX that acts as a gateway --> That same box has squid installed and
filters the http request (Normal ACLs) --> Depending on the private IP
of the user the r

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