Site-to-Site PPTP VPN connection between two Windows Server 2008 R2 servers
- by steve_eyre
We have two Windows Server 2008 R2 machines, one in our main office and one in a new office which we have just moved offsite. The main office has previously been handling client-to-server PPTP VPN connections.
Now that we have moved our second server out of office, we want to set up a demand-dial or persistent VPN connection from the second server to the primary. Using a custom setting RRAS profile, we have successfully managed to set up a site-to-site VPN connection so that from the second server itself, it can access any of the devices in the main office and communicate back. However, any connected machines in the second office cannot use this connection, even when using the second server as gateway.
The demand-dial interface is setup from the Second Server dialing into Main Server and a static route set up on RRAS for 192.168.0.0 with subnet mask 255.255.0.0 pointing down this network interface.
The main office has the network of 192.168.0.0/16 (subnet mask 255.255.0.0).
The second office has the network of 172.16.100.0/24 (subnet mask 255.255.255.0).
What steps do we need to take to ensure traffic from the second office PCs going towards 192.168.x.x addresses use the VPN route? Many Thanks in advance for any help the community can offer.
Debug Information
Here is the route print output from the second server:
===========================================================================
Interface List
23...........................Main Office
22...........................RAS (Dial In) Interface
16...e0 db 55 12 fa 02 ......Local Area Connection - Virtual Network
1...........................Software Loopback Interface 1
12...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter
14...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter #2
24...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter #3
===========================================================================
IPv4 Route Table
===========================================================================
Active Routes:
Network Destination Netmask Gateway Interface Metric
0.0.0.0 0.0.0.0 172.16.100.250 172.16.100.222 261
127.0.0.0 255.0.0.0 On-link 127.0.0.1 306
127.0.0.1 255.255.255.255 On-link 127.0.0.1 306
127.255.255.255 255.255.255.255 On-link 127.0.0.1 306
<MAIN OFFICE IP> 255.255.255.255 172.16.100.250 172.16.100.222 6
172.16.100.0 255.255.255.0 On-link 172.16.100.222 261
172.16.100.113 255.255.255.255 On-link 172.16.100.113 306
172.16.100.222 255.255.255.255 On-link 172.16.100.222 261
172.16.100.223 255.255.255.255 On-link 172.16.100.222 261
172.16.100.224 255.255.255.255 On-link 172.16.100.222 261
172.16.100.225 255.255.255.255 On-link 172.16.100.222 261
172.16.100.226 255.255.255.255 On-link 172.16.100.222 261
172.16.100.227 255.255.255.255 On-link 172.16.100.222 261
172.16.100.228 255.255.255.255 On-link 172.16.100.222 261
172.16.100.229 255.255.255.255 On-link 172.16.100.222 261
172.16.100.230 255.255.255.255 On-link 172.16.100.222 261
172.16.100.255 255.255.255.255 On-link 172.16.100.222 261
192.168.0.0 255.255.0.0 192.168.101.87 192.168.101.17 266
192.168.101.17 255.255.255.255 On-link 192.168.101.17 266
224.0.0.0 240.0.0.0 On-link 127.0.0.1 306
224.0.0.0 240.0.0.0 On-link 172.16.100.222 261
224.0.0.0 240.0.0.0 On-link 172.16.100.113 306
224.0.0.0 240.0.0.0 On-link 192.168.101.17 266
255.255.255.255 255.255.255.255 On-link 127.0.0.1 306
255.255.255.255 255.255.255.255 On-link 172.16.100.222 261
255.255.255.255 255.255.255.255 On-link 172.16.100.113 306
255.255.255.255 255.255.255.255 On-link 192.168.101.17 266
===========================================================================
Persistent Routes:
Network Address Netmask Gateway Address Metric
0.0.0.0 0.0.0.0 192.168.0.200 Default
0.0.0.0 0.0.0.0 172.16.100.250 Default
===========================================================================
IPv6 Route Table
===========================================================================
Active Routes:
If Metric Network Destination Gateway
1 306 ::1/128 On-link
16 261 fe80::/64 On-link
16 261 fe80::edf4:85c6:3c15:dcbe/128
On-link
1 306 ff00::/8 On-link
16 261 ff00::/8 On-link
22 306 ff00::/8 On-link
===========================================================================
Persistent Routes:
None
And here is the route print from one of the second office PCs:
===========================================================================
Interface List
11...10 78 d2 32 53 27 ......Atheros AR8151 PCI-E Gigabit Ethernet Controller
1...........................Software Loopback Interface 1
12...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter
13...00 00 00 00 00 00 00 e0 Teredo Tunneling Pseudo-Interface
===========================================================================
IPv4 Route Table
===========================================================================
Active Routes:
Network Destination Netmask Gateway Interface Metric
0.0.0.0 0.0.0.0 172.16.100.250 172.16.100.103 10
127.0.0.0 255.0.0.0 On-link 127.0.0.1 306
127.0.0.1 255.255.255.255 On-link 127.0.0.1 306
127.255.255.255 255.255.255.255 On-link 127.0.0.1 306
172.16.100.0 255.255.255.0 On-link 172.16.100.103 266
172.16.100.103 255.255.255.255 On-link 172.16.100.103 266
172.16.100.255 255.255.255.255 On-link 172.16.100.103 266
224.0.0.0 240.0.0.0 On-link 127.0.0.1 306
224.0.0.0 240.0.0.0 On-link 172.16.100.103 266
255.255.255.255 255.255.255.255 On-link 127.0.0.1 306
255.255.255.255 255.255.255.255 On-link 172.16.100.103 266
===========================================================================
Persistent Routes:
None
IPv6 Route Table
===========================================================================
Active Routes:
If Metric Network Destination Gateway
1 306 ::1/128 On-link
11 266 fe80::/64 On-link
11 266 fe80::e973:de17:a045:aa78/128
On-link
1 306 ff00::/8 On-link
11 266 ff00::/8 On-link
===========================================================================
Persistent Routes:
None