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What would be the best way (i.e., most reliable way) to create a persistent VPN connection between 2 servers if you don't have the ability to create a point to point VPN between the edge firewalls/routers of the 2 networks?

I have a server that's geographically distant from our office (for example, say the office is in San Diego and the remote server is in Chicago). We do not control the firewall/router for the remote location. We need the remote server to maintain a persistent VPN connection back to our offices. By persistent, I mean connects automatically (even after reboots), doesn't time out, and can re-connect in the event of a dropped connection. The remote server will be a member of our domain (all Domain Controllers are in the office location). Only traffic for the domain's subnet should go over the VPN connection. All other traffic should otherwise go to the remote server's default gateway.

We do have a VPN Server at the office location (Windows Server 2003 RRAS). The remote server is Server 2008. I do have control over the office firewall, but not the remote firewall or router. Is there any robust/reliable way to set this up?

Hopefully the description makes sense. If more detail is needed, please ask.

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Have you tried playing around with something like OpenVPN? I'd think that with a little bit of scripting it might not be too hard..

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I have always been a huge fan of point to point VPN appliance from the likes of Cisco, Sonicwall, Juniper, etc. You say ou dont have access to the remote router, but that doesn't mean you cant layer another commodity firewall appliance on top of theirs.

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Its a hosted remote server, so I have no physical access whatsoever :( I'd give anything to set up a point to point via hardware, but its not an option. – zona Aug 19 '09 at 22:57
In this case, definitely look at OpenVPN – prestomation Aug 21 '09 at 3:29

OpenVPN has my vote. It is free and works really well.

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