I'm having trouble to figure out something that Microsoft changed from Win 2003->2008 VPN. This is my setup:

office #1

subnet #1:  
subnet #2:
Windows 7 as VPN client

office #2

subnet #1:


  1. A Windows 2008 Server with VPN/RRAS installed is in office #2. After connecting from office#1/subnet#1 to office #2/subnet#1 I cannot ping or access anything in office#1/subnet #2 from office#1/subnet#1 route print shows that a route is added

  2. Windows 2003 Server VPN/RRAS installed in the office #2: everything works fine

Any idea how to make it work?


See KB254231.

This is how Windows unfortunately now handles routes when given an IP via PPP. It decides to put a route in by its self and guess the subnet mask based on the old clasful system. Terrible pain the rear this is.

Cheers, Gavin.


It looks like your VPN config is pushing a route for to the clients. This means that all of your traffic for office 1 subnet 2 is attempting to traverse your VPN instead of staying local. To fix this, you should configure the route being pushed to your clients to be so that it matches the subnet at the remote site.

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