OpenVPN Nested Chain Through VirtualBox: Can Ping But Cannot Access The Web



  • I'm using VirtualBox to create a nested VPN chain. For simplicity purposes, I created two PFSense VMs configured with OpenVPN, one named VPN1 and the other VPN2.

    On their own, both these routers work properly and load web pages as well as successfully passing through the VPN. Both these routers configured with the same VPN provider and pings 8.8.8.8 in about 250ms.

    In VirtualBox's VM settings, for VPN1 and under Network, I choose NAT as network adapter 1 and internal network "Int_1" for network adapter 2. For VPN2, I choose "Int_1" for network adapter 1 and internal network "Int_2" for network adapter 2. I then take a virtual machine with Linux installed on it and connect it's network adapter 1 to internal network "Int_2". So the VM where the browsing occurs is connected to VPN2, which is connected to VPN1, which is connected to NAT.

    When combined, these two routers seem to be somehow connecting. In VPN2's console and in the browsing VPN, I can ping 8.8.8.8 at an expected 500ms (2*250ms), however, I seem to be unable to load web pages. For example, trying to load google.com gives me the "Server not found" error message, and the further the "connecting…" notification thing goes is telling me "Looked up google.com...".

    To sum it all up: both VPN routers work flawlessly as standalones, but when connected to each others as a chain through VirtualBox's internal networking, they can ping but can't load web pages.

    It may help to know that I do not allow DNS server list to be overridden by DHCP/PPP on WAN. I followed the general PFSense instructions given by NordVPN (https://nordvpn.com/tutorials/pfsense/pfsense-openvpn/)


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