VPN oddity

canooten

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I've got an oddity with my work VPN connection. Hoping someone has some things I can try.

I've got a PPTP VPN powered by a SBS2003 machine. Pretty much default settings down the line on the SBS machine.

Users connect with the Windows VPN client and most connections are strictly for accessing a single Linux server on the network. Problem is that the server is usually not reachable on the VPN when you connect.

Normal process goes something like - connect to VPN, ping IP address of server, no reponse, disconnect from VPN, reconnect to VPN, ping IP address of server. Rinse and repeat until you get a response, then you can connect to the machine. Connection is rock solid once the IP address is visible over the VPN. Sometimes it only takes a couple of attempts, sometimes it's 30. Eventually it'll show up, but it's a total crapshoot on how big an ordeal it is to connect.

Odd thing is that all other devices/IP's on the network are visible over the VPN . Even the 2nd NIC on the same server is always reachable, just not this one IP, which happens to be the one we need 98% of the time .

I'm sure I'm leaving out plenty of necessary info, so ask away and I'll fill in as many blanks as I can.
 
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