Although you technically can do this (although the middle and exit would no longer really be considered bridges, and you couldn't connect to hidden services without using a public rendezvous), it is a horrible idea. Bridges are to hide the fact that you use the Tor network. You don't want to be the only person using all of the nodes on your path, and you don't want all of the nodes on your path to be linkable back to you. Stick with just using single node entry bridges. Using two entry bridges is a very good idea, but leave that for the Tor project to implement, because unless everyone is doing it (and 4 hops total are being used) it will hurt your anonymity more than hep. Bridges are only concerned with a local attacker being able to determine that you use Tor, remote attackers still know you are using Tor as you exit from a publicly listed exit node, as you should. Obfsproxy obfuscates the traffic fingerprint associated wtih Tor. Normal bridges give you membership concealment by hiding the fact that you are connecting to a Tor router IP address, as the IP addresses of bridges have limited exposure (or no exposure if they are private and you configured them yourself). This prevents or hinders many weaker attackers (like your ISP most likely, or network admin of your network) from being able to determine that you are connecting to a Tor router based on the IP addresses that they see you connecting to (sort of, there are still ways around it, bridges are developing technology not perfected. For starters an attacker could try and use every IP address they see you connecting to as a Tor bridge and see if it works. But that still requires them to target you in the first place, and how will they know who to target since they don't know bridge IP addresses? I think this flaw is being worked on anyway.) However, Tor traffic has a very distinct fingerprint. For one example out of several, all packets are 512 bytes plus headers. This is not the same for most internet traffic. So even though an attacker may not be able to tell that you are using Tor based off of the IP addresses they can see you connecting to, they can still tell that you are using Tor by analyzing your traffic stream. Obfsproxy takes care of this by obfuscating the traffic stream, trying to make it blend in with other traffic and not stick out as Tor traffic. Certainly setting up your own private obfs bridge is the best option for membership concealment. Either should be fine. No you should use a private obfsproxy bridge for entry and exit through a normal Tor exit, although in some circumstances using a Tor exit may not work (like working with some shitty e-currencies / exchangers) and in these cases it is okay to chain a VPN to the end of a Tor circuit, but this does more to hurt your anonymity than to help it (for one it makes things much more linkable, although it may help your untraceability somewhat) Not sure what you mean. I doubt it is really using only 3 or 4 relays, but yes that would not be safe.