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I'm tinkering with web servers on Rackspace, trying to figure out if I can set up a website with public parts and also private parts that are visible only via a VPN connection.

I have 2 servers running apache, the first has a mixture of public and private sites. The second has private sites and also pptpd running as the VPN server. In both cases, the internal IPs (10.n.n.n) are exposed via DNS for the private sites.

Here's a hastily drawn diagram that should hopefully show how I've managed to rig things:

network diagram

The public sites work fine. The VPN connection works fine. The private sites on server 2 work fine when connected to the VPN. What doesn't work is accessing the private sites on server 1 via the VPN. I've added a potentially misleading red arrow to the diagram showing where I think the problem is.

I can ping each server from the other on their internal addresses, and I can ping server 2 over the internet on its internal address. What I can't do is ping server 1 over the internet.

I feel that I'm naively missing some essential networking knowledge about how VPNs actually work. Can anyone see what I'm missing?

Here's the internal IP address information

Server 1
    inet addr:10.177.129.10  Bcast:0.0.0.0  Mask:255.255.192.0

Server 2
    inet addr:10.176.132.180  Bcast:0.0.0.0  Mask:255.255.192.0
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Are both of the private IPs on the same subnet as the IP that is being assigned by the VPN server to your client? –  Garrett May 4 '12 at 23:33
    
Since even ping doesn't work, can you take Apache out of the question and diagram and instead label the nodes with IP addresses? –  ckhan May 6 '12 at 4:01
    
I've added the internal IP address info –  izb May 6 '12 at 8:07

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