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We are running PFSense 2.0.1-RELEASE and need to make the following scenario work: 1..n remote offices for company A need to connect to a private VPN (VPN server hosted in our datacenter). All the devices in all the remote offices need to be on a single subnet and be able to talk to each other.

This is not a problem with the VPN server in PFSense, with a single company. The problem is company B. They have to have a private VPN, and private subnet also. I don't see a way of creating a second PPTP VPN server in PFSense.

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Never use PPTP for site to site VPNs, use IPsec or OpenVPN. It's also pretty much never a good practice to put multiple locations on the same subnet, each should have its own unique subnet with routing between them over the VPN.

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