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?