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I have a Server 2008 R2 machine connected to 2 networks with its 2 network cards.


I have a site-to-site VPN with the following network layout:


For some reason whenever my server pings the VPN network it times out most of the time. Machines on my LAN that aren't connected to the SAN have no problem communicating with the VPN. If I disable the SAN network card on the server, it also has no problems communicating with the VPN network.

I've attempted to add a static route to ensure traffic passes through the LAN interface to reach the VPN network but it worked for 2 ping attempts then stopped. Here's my routing table:

    Interface List
     12...00 50 56 aa 00 03 ......Intel(R) PRO/1000 MT Network Connection #2
     10...00 50 56 aa 00 02 ......Intel(R) PRO/1000 MT Network Connection
      1...........................Software Loopback Interface 1
     11...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter
     13...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter #2

    IPv4 Route Table
    Active Routes:
    Network Destination        Netmask          Gateway       Interface  Metric
           On-link    306
           On-link    306         On-link    306
         On-link    266         On-link    266         On-link    266     11         On-link    266         On-link    266         On-link    266
           On-link    306
           On-link    266
           On-link    266         On-link    306         On-link    266         On-link    266
    Persistent Routes:
      Network Address          Netmask  Gateway Address  Metric

    IPv6 Route Table
    Active Routes:
     If Metric Network Destination      Gateway
      1    306 ::1/128                  On-link
      1    306 ff00::/8                 On-link
    Persistent Routes:

I'm attempting to define it so that any time 192.168.4.X needs to be reached, the packets will be sent to which is my SonicWall router where the VPN is connected. What am I doing wrong?

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Get rid of the Default Gateway on the SAN NIC. – joeqwerty Jan 30 '14 at 18:57
up vote 1 down vote accepted

Stick to one default gateway, and then add your static routes based on which gateway you go with. So if you keep the as your Default Gateway and remove the you'll need to add routes for any subnet that isn't directly connected to that network you have direct access to if you want to reach it via that NIC.

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I have no idea why the network also has a default gateway assigned. Windows did that on its own. I guess I need to delete it then. How do I make this change persistent? – user207539 Jan 30 '14 at 17:35
If it is getting a DHCP address, you can't. You have to assign the IP statically and then not set a Default Gateway on that NIC. – TheCleaner Jan 30 '14 at 19:22
It wasn't using DHCP. Solved it myself with: route delete route add route add -p – user207539 Jan 30 '14 at 19:53

The problem is that you have two default gateway here. I answered a question just like that a day or two ago.

Setting a static route for a specific network adapter with two network adapters

What you want to do is to have only one of the two network adapter with a default gateway. At that point, all traffic for other network will route through that adapter which has the default gateway.

If you then want to route 192.168.4.x through the other interface, you can add a route that sends that traffic to the gateway of your choice. If that gateway is on the same subnet as your interface which does not have a default gateway defined, then it will go through that interface.

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