I'm having a bit of trouble routing my traffic through my VPN server. Basically I have a pfSense setup that works amazingly well for everything it's currently doing. However, now, I have need to set up a PPTP VPN. I've got the basic setup and login working fine. When I check my IP it says I'm on the remote network, etc. However, I can't seem to figure out how to properly route traffic to the internal network.

My current setup is as follows:

Trendnet Router:
1 MAC (
1 PC(


pfSense Firewall:
7 PC
3 Linux
all on subnet

Server Address:
Remote Address Range:
Require 128-bit Encryption:  True

As I said, I can connect to the PFSENSE VPN just fine and I'll receive an IP of (or above). However I need to figure out what kind of rules I need in order to route traffic to the machines on the WORK subnet so that they show up in network neighborhood, etc (and so that I can eventually VNC to them). I've added a rule to allow ALL traffic from the PPTP interface in, but I'm not sure where to go from here. Any assistance is most appreciated.


You're work and home networks are setup on the same subnet ( You are going to need to switch one of them to another subnet otherwise the machines will never be able to route out to the machines on the other network, as they think they are local.

If you still can't talk after you switch the subnet at one location, post back here and we can work with you from there.

To clarify a little on how VPN works based on your comment.

You don't assign the VPN clients to the same subnet as you office. They need to be on a unique subnet. For my example lets assume the following:

  • Home subnet is
  • Office subnet is
  • VPN subnet is

What a connection to the office would look like is this:

  • Home computer: NIC1:; vNIC1-VPN:
  • pfSense: PublicNIC:; PrivateNIC:; vNIC1-VPN:
  • office server: NIC1:

The vNICx-VPN nics will be setup by your vpn client/server

After the user has established a VPN connection to the office, the traffic flow will look like:

The Home Computer connects to it will:

  1. Look up the route in the routing table
  2. see a route that specifies the VPN adapter as the gateway
  3. The VPN Client subsystem will encapsulate the packets
  4. The machine will then send them over the public internet to the pfSense router.

Once the router gets a VPN encapsulated packet it:

  1. sends it to the VPN Daemon subsystem
  2. The VPN subsystem will decode the packet
  3. The host will look up the unencrypted destination
  4. The machine will then route it out the proper interface to be sent to the Server.

The response from the server will be sent to the pfSense router (since the subnet is not directly connected and the machine doesn't have any routes to that machine)

The pfSense router will:

  1. look up the Home computer VPN IP as that is what the server will see the packet as comming from.
  2. The routing table will tell it to send it through the VPN virtual adapter.
  3. The packet will be sent to the vpn Subsystem encapsulated, and sent over the internet to the client machine.

Once at the client machine the VPN subsystem will decrypt the packet and send it up the networking stack to the application.

Wash, rinse, repeat.

  • Can I not "cross-route" with some specialized rules? Unfortunately I cannot change every employee's home subnet so as to be compatible with the work subnet. Nor can I change the office setup at this point in time. Is there anything else I can do? – humble_coder Jan 7 '10 at 2:08
  • The problem is that you would potentially need to push the "cross-route" to the client machines as well were it even possible. Assuming this were even possible (which it isn't) - how on earth would you handle IP address collisions (home computers and work computers with the same IP address). This just isn't going to work without changing the network. I would recommend changing the work network - probably to something in the 10.x.y.z range. – Goyuix Jan 7 '10 at 3:21
  • 1
    @huble_coder: No, Connected routes take precedence that is why most companies try to avoid the, and ( the most common home networks ). A or would be most preferable. If you want to saty then go with something like – Zypher Jan 7 '10 at 5:24
  • Alright, I will beg borrow and steal today in order to get approval for office IP change. That said, once I have them on a different subnet, I still face the challenge of not being able to assign the VPN clients to the same subnet as the office -- pfSense warns me that the address range I've chosen for VPN clients is in the same subnet as the office. So, how do I proceed from there? – humble_coder Jan 7 '10 at 15:35
  • Ok so I got the office switched to Everything works like a charm--mostly. I can map, ping, and manually mount remote drives. However it seems that no NETWORK NEIGHBORHOOD, or "zero-config" items work. Do I need to set up a rule to pass all traffic on the network (or maybe just UDP)? – humble_coder Jan 14 '10 at 16:40

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