I have somewhat of an odd setup for a VPN server with OS X Mountain Lion. It's essentially being used as a bridge to bypass my company's firewall to our extranet connection - certain things our team needs to do require unfettered access to the outside, and changing IT policies to allow traffic through the main firewall is just not an option.

The extranet connection is provided through a Wireless-N router (let's call it Wi-Fi X). My Mac Mini server is configured with the connection to this router as the primary connection, thus unfettered access to the internet via the router. Connections to this device on the immediate subnet are possible through the LAN port, but outside the subnet things are less reliable.

I was able to configure the VPN server to provide IP addresses to clients in the 192.168.11.150-192.168.11.200 range using both PPTP and L2TP, and I'm able to connect to the extranet through the VPN using the standard Mac OS X VPN client in System Preferences, however unsurprisingly, a local address (let's call it internal.company.com) returns nothing.

I tried to bypass the limitation of the VPN Server by setting up Routes in the VPN settings. Our company uses 13.x.x.x for all internal traffic, instead of 10.x.x.x, so the routing table looked something like this:

IP Address ---------- Subnet Mask ---------- Configuration
0.0.0.0               248.0.0.0              Private
8.0.0.0               252.0.0.0              Private
12.0.0.0              255.0.0.0              Private
13.0.0.0              255.0.0.0              Public
14.0.0.0              254.0.0.0              Private
16.0.0.0              240.0.0.0              Private
32.0.0.0              224.0.0.0              Private
64.0.0.0              192.0.0.0              Private
128.0.0.0             128.0.0.0              Private

I was under the impression that if nothing was entered here, all traffic was routed through the VPN. With something entered, only traffic specifically marked to go through the VPN would go through the VPN, and all other traffic would be up to the client to access using its own default connection. This is why I had to specifically mark every subnet except 13.x.x.x as Private.

My suspicion is that since I can't reach the VPN server from outside the local subnet, it's not making a connection to the main DNS server and thus can't be reached on the larger network. I'm thinking that entering hostnames like internal.company.com aren't kicked back to the client to resolve, because the server has no idea that the IP address falls in the public range, since I suspect (probably should ping test it but don't have access to it right now) that it can't reach the DNS server to find out anything about that hostname.

It seems to me that all my options for resolving this all boil down to the same type of solution:

Figure out how to reach the DNS with the secondary connection on the server. I'm thinking that if I'm able to do [something] to get my server to recognize that it should also check my local gateway (let's say Server IP == 13.100.100.50 and Gateway IP == 13.100.100.1). From there Gateway IP can tell me to go find DNS Server at 13.1.1.1 and give me information about my internal network. I'm very confused about this path -- really not sure if I'm even making sense.

I thought about trying to do this client side, but that doesn't make sense either, since that would add time to each and every client side setup. Plus, it just seems more logical to solve it on the server - I could either get rid of my routing table altogether or keep it - I think the only difference would be that internal traffic would also go through the server - probably an unnecessary burden on it.

Any help out there? Or am I in over my head? Forward proxy or transparent proxy is also an option for me, although I have no idea how to set either of those up. (I know, Google is my friend.)