My uni logs data traffic and I have 100GB per month. At first, I only wanted to bypass uni servers to avoid being banned. Besides, I'm testing some OSs to absolutely clean install a new system and the more I'm into it, the more it catches me.

My host is Windows 7 Professional 64bit using VMware Player or Virtualbox (more familiar with VMware) and the software shared by the VPN provider. [Means: no PuTTY or FoxyProxy things, no shell code (in Win7 at least). Easy software which monkeys like me are able to use without any solid knowledge base in network engineering.] Guests installed are Win7 Ultimate, Kubuntu,
Win7 Ultimate N, Ubuntu, Tails, Linux Mint, ArchLinux, Antergos. (Haven't found the right one yet)

The question is concerning the setup Win7P (host OS) ↔ Win7U (guest OS).

The host's internet connection is established through an SSH-tunnel inside a VPN. For all HTTP, SOCKS5 and TOR data traffic a proxy is set up also tunneled through the VPN to the provider's proxy servers. In other words and according to netstat -n, I connect from my 192.168.host:port to VPN:22. On the VPN server I get a new internal IP, let's say 172.168.host. Then 172.168.host connects to Proxy:22.

After all the loops for example my TOR connection basically is:
Host <-> 5003: <-> ssh:VPN server:someport <-> ssh:Proxy server:exit-to-tor

When I choose NAT in VMware as network adapter traffic obviously isn't channeled through the proxy connection since the IPs are located in different cities. Assuming the connection is:
Guest <-> VM network adapter <-> 192.168.host <-> ssh:VPN:exit

How can I make the guest use the host's proxied channel?

Or can I let the host listen to the ports I assign to the guest's data traffic?
Is this possible without installing a VPN between host and guest or using a second VM with a server connecting them?

Using the bridged apapter gives me, so no connection to the internet at all. VMnet0 (auto-bridging) lets the guest imitate a second computer in the usual home network 192.168.0.x. Via VMnet1 (host-only) again there's nothing.

The only entry in netstat -n showing VM IPs is the one from the VM to the guest's SMB port 445 (in netstat -f it says microsoft-ds).

I found out that the host cannot access the guest using NAT. Somehow I could access guest's shared folders, although ping did work only from guest to host. Further I found out (in the documentations and in fora) that the host can route its traffic through the guest.

Of course I simply could install the VPN & Proxy software on the guest OS, but this solution seems not clean enough to me. I'd like to have one straight line of data traffic.

Somehow VMware and Virtualbox haven't considered implementing this. In Virtualbox I only found how to set up the NAT configuration to redirect traffic from host to guest.

  • You are aware that using a VPN/ssh-tunnel won't help you with your 100 GB limit, right? You won't be "bypassing" university servers; your network traffic will still go through them, it'll just be encrypted. – jamesdlin Feb 17 '18 at 2:09
  • Our residence hall network admin told me that our uni servers’ firewalls have problems logging VPN usage so they don’t log the traffic at all – mrfinch Feb 18 '18 at 21:11

Try installing a VM of pfsense to handle DHCP for your network. Then set up a virtual bridge for other VMs to connect to pfsense. Then set up a vpn on pfsense to forward all traffic thru the vpn. I set this up once for Whonix.

  • pfsense sounds really nice and I definitely will try it out. Since I have many important stuff to do in the next 2-3 weeks I hoped to get a solution that can be achieved with the tools I already have and mainly by clicking... Can VMware’s FLEX Server do this job too? Haven’t installed it yet – mrfinch Feb 15 '18 at 21:45

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