I have tested it and it works fine, although there is higher latency. I have not done an in depth analysis of the anonymity properties, but the only problem I can imagine would be if T1 and T2 re-use nodes between them. Even that wouldn't be horrible for a hidden service, considering the entry guard can already trivially determine if it is an entry guard for any given hidden service. You might not even need to protect from node reuse for hidden services, although if you were a normal client it would be important to do so because you would definitely not want to reuse the same node for entry and exit in that case. I would bet five hundred bucks that configuring a hidden service to use two instances of Tor in this way would extremely increase the anonymity provided. As it stands today, tracing hidden services is trivial. You can trace to each of a hidden services entry guards in under a minute, and then it is just a matter of either forcing it to change to new entry guards until it picks one of yours, or if you are a stronger attacker simply sending a court order to one of the entry guards or its infrastructure. A hidden service with an entry guard in USA could realistically be deanonymized in a couple of hours if the feds had a fucking clue. If LE actually had a clue they wouldn't even need to spend much effort to trace hidden services. If I had the powers of even a low ranking federal agent I could certainly deanonymize any 'out of the box' configured hidden service. It is simple. Hopefully they actually know what they are doing if they always change servers, it would be a waste of time to change the location of the server without rotating all of its entry guards. But the time frame they will have to switch the server to a new location is very small, hidden services can be traced very quickly by moderately powerful attackers (and FBI has legal powers that put it well within this range, even if their technical people are dumb shits) It can be done with no downtime at all very easily. I doubt that they want anything to do with anyone who has such a resume .