Is there possibility of using Tor via Tor


Now I have two options. First is running Tor browser.
Second is work through Tor in virtual machine (host system shares Tor to virtual machine via
virtual network adapter).

Virtual machine is VMWare, virtual network adapter is Tortilla.

Question is. Is there possibility of using Tor via Tor Browser in that virtual machine? Tor over Tor?

Tor over Tor?

that’s explicitly blocked by the network as it’s a fairly easy vector for a denial of service (connect to tor through tor through tor through tor… and everything you do cost N time more than it should).
Whonix provides the kind of isolation you seems to be seeking. You can try to use that, or to look at how they made it work. I think it’s about configuring TorBrowser so it uses the tor outside the VM, and not the tor it bundles.

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In what way?

Exit nodes don’t allow reentry in the network. So when TB tor asks to connect to my_guard_ip:my_guard_port, the outside-of-VM tor won’t be able to find an exit node that let it connect to TB guard.

Wouldn’t setting a bridge work?

Just tested - does not work:
tor running and providing socks5 proxy for a second tor trying to use an obfs4 bridge.

@trinity-1686a | But I hope the bridge enforces this - not the exit - otherwise all exits know all the bridges?

Even if it did work, it wouldn’t be safe.

In fact, years ago there was no such protection, and you had to be careful to avoid accidentally running Tor over Tor. From what I remember, the reasoning was that the two instances could inadvertently build a 6-hop circuit that shares relays of the same family, subnet, country, or even the same node. The best example being where the inner Tor’s exit node is the same as the outer Tor’s entrance (guard) node, effectively making it a 1-hop circuit.


Method 1: Tor over Orbot

Step 1: Install Orbot (MacOS/iOS/Android only)
Step 2: Before connecting to Tor via Orbot, close TBB.
Step 3: After connecting to Orbot, launch TBB. It will fail to connect. This is normal. Simply click “use a bridge” and it should work.

Tested: MacOS Sonoma 14.2.1 + TBB 13.0.8 + Orbot 1.6.6. Works, but is slow, but that’s to be expected.

Method 2: Tor over little-t-tor

Step 1: Install little-t-tor. MacOS/Linux instructions/ Windows instructions (Stackoverflow)
Step 2: Start little-t-tor
Step 3: little-t-tor should listen on over port 9050. Go to TBB > Settings > Connection > Advanced > Configure how Tor Browser connects to the Internet > I use a proxy to connect to the Internet. Set “Proxy Type” to SOCKS5; “Address” to; and “Port” to 9050.
Step 4: Use a Obfs4 bridge and connect. Done!

Tested: MacOS Sonoma 14.2.1 + TBB 13.0.8 + little-t-tor Works, but is unstable.