I've been trying to follow this tutorial: the goal is to have all connections made from my debian virtual machine, pass through Tor installed on my ubuntu host machine. The host machine is a freshly installed Xubuntu 14.04 running virtual box.

I have followed each step of the tutorial as well as all the variants found around the web.

My VM successfully obtains an IP in the expected range but when I try to ping a host, after correctly resolving its IP address, the packets get invariably lost.

This is my HM route table:

Destination     Gateway         Genmask         Flags Metric Ref    Use Iface         UG    0      0        0 wlan0     U     1000   0        0 vnet0   U     0      0        0 vnet0   U     9      0        0 wlan0

My HM ifconfig vnet0:

vnet0     Link encap:Ethernet  HWaddr 66:4e:0b:d9:d8:26  
          inet addr:  Bcast:  Mask:
          inet6 addr: fe80::644e:bff:fed9:d826/64 Scope:Link
          RX packets:0 errors:0 dropped:0 overruns:0 frame:0
          TX packets:91 errors:0 dropped:0 overruns:0 carrier:0
          collisions:0 txqueuelen:0 
          RX bytes:0 (0.0 B)  TX bytes:11165 (11.1 KB)

My VM route table:

Destination     Gateway         Genmask         Flags Metric Ref    Use Iface         UG    0      0        0 eth0     U     1000   0        0 eth0   U     0      0        0 eth0

After encountering other problems I manged to get this far with the little knowledge I gained from a networking course followed at Uni, but from now I really wouldn't know where to head even to start debugging the problem.

Could you please help me out?


If you're not using automatic host mapping, there will be no ping : Tor transparent proxy and SOCKS proxy are TCP tunnels only, no ICMP or UDP.

And the tutorial is VERY weird, IMHO. Try to use TransPort as a divertion target, as it supposed to be used.

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The first things, I usually check,when I have this kind of problems, are:

  1. /etc/resolv.conf
  2. verify, if used, firewall rules
  3. use a traceroute command to follow the path done from your data
  4. I give as sure you already verified, but if not check correct gateway configuration

Usually the first point is the goal: a lot of people forget to setup correctly the resolv.conf file !!

The second point can be easily cheched: simply shut down your firewall ad verfiy if connection works. If it's the case sure the problem is a firewall rule;

The third point can help you finding where your data is blocked or lost.


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  • thanks for the answer; I had tried points 1,2 and 4 without success. Did not try the 3rd which seems the most "universal". However I have now opted for a different solution and I am unable to go back to the middlebox project in order to verify where the problem was. – sowdust May 27 '14 at 19:54
  • I'm sorry that you give up for one problem your project: I think you should groped to solve it; at least you would have learned what was wrong for a possible next time :) A.G. – AnteGamissu May 28 '14 at 7:13

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