Static Route - other gateway with proxy

[mynullvoid]

My pfsense is acting as a gateway, but I also have another gateway if the destination IP matches some IP I stated. The problem I got is that that another gateway requires traffic to pass a proxy server:port, can the version 2 do it?

[jimp]

If that proxy can act transparently, it might be possible to add a NAT rule which would match the traffic heading to that subnet and direct web access heading that way into the proxy.