Server Timeout

[nolesce]

We have an IIS server serving a couple of asp based sites to the internet while still connected to our network and VPN. The server has 2 NICs and static routes set up to keep traffic straight. Problem is that since the static routing was activated about 2-3 times a day the sever becomes unreachable from the internet. Resetting the router fixes this but is only reactive. I did a little sniffing and the ONLY http traffic I see when the server is 'not connected' is a "GET /http 1.1 request" from the server and an "Authorization Required" response from the router. Any thoughts?