Virtual Private Servers are getting fairly cheap, and Amazon EC2 instances even cheaper. A hundred or so dollars per month could put together a fairly large set (say, five ?) of general purpose unix nodes on at least 3 continents ... EC2 in Asia and Ireland, and then some bullshit VPS provider(s) here and there in the US. So let's say you assemble a little quiver of these root shells, and your intention is to completely obfuscate your own personal traffic ... to just disappear completely (as an atomic, individual net user). The technical foundation is pretty basic - just set up your own system, or perhaps a firewall at your home/office to block all traffic except for SSH or HTTPS and to take all outbound traffic and tunnel it over one of those to a random one of your systems. Easy. ----- So at this point, what do you have ? First, your own ISP no longer sees anything but encrypted traffic. I suppose they also see time patterns, but you've pretty much excluded your own ISP from all information regarding your net usage. Further, you've upped the ante considerably - an actor has to have a global eye view of the entire global Internet to collect a true portfolio of your net usage. Maybe a few US nodes are easy, and maybe if you go EC2 Ireland, that's easy too ... but some VPS provider in Hong Kong ? Seoul ? Sao Paulo ? ----- So where does this start to fall apart ? First, if you hit any kind of personal/vanity/small sites on a daily or hourly basis, an attacker just has to camp out upstream from there and collect all the source IPs that come in. So if you run your own mailserver (or whatever), this falls apart almost immediately. You either need to start hosting a lot more traffic on your own server (giving away accounts or something like that) or you need some kind of jumphost that isn't connected to you, and an out of band link between the jumphost and your own site(s). This isn't rocket science, though ... just set up a big ubuntu/freebsd/whatever mirror next to your own vanity host, and cross connect with an ethernet cable over non routable IP space. Second, unencrypted login sessions ... between web forums and chat rooms and any number of other things, somewhere you're entering a user/pass over plain old HTTP... and if an attacker can guess one or more sites that they know you visit, they can, just like above, camp out upstream and just collect all of your proxy IPs. This is easy to fix with a firewall rule, but may be impractical to deal with that way ... a certain discipline with nyms and aliases, etc., needs to be adopted, and unlike typical "nym leakage" you need to be thinking of nym leakage on an infrastructure level. Not impossible, though... Where else does this fall apart ? I don't think there is a weakness with DNS resolution, since the dns resolution will come from your proxy, which will move around... presumably your local connection has everything but 22 (or 443) blocked. Remember, this isn't Tor ... the idea here is not to create mathematically provable security. The idea is to make ones own traffic disappear to a degree that one needs to be a nation state to put it back together. The local ISP can't see it, the servers you visit can't see it, and the intermediate ISPs (and even a conglomeration of several of them) can't see it. And it looks like this is a fairly cheap thing to put together in 2010...