This is an arms race. Unlike the crypto arms race, which eventually goes to the cryptographer, I don’t know who this arms race goes to. The proposed evasion technologies seem all to require some other party to initiate a proxy service to redirect queries from the citizen whose web access is limited by an ‘oppressive government’ (OG). As OG discovers the identities of such specific evasion sites they too may be blocked. OG learns of these sites the same way that the intended users do. The ‘good news’ is that it is easy to set up these proxy servers. The ‘bad news’ is that dissemination of the identities of these new sites leaks to OG nearly as fast as to the intended users. Presumably such identity information travels by a spanning tree of intended users. Some of the links in the tree are via cyberspace, some by POTS and some by voice or mail. The links of this tree are, of course, of high interest to the OG. The ‘leaks’ in the tree are of high interest to the ‘legitimate’ members of the tree. The logic of this information battle has not changed much in the last few thousand years except perhaps for the time scale. A classic tool of the tree defender is to limit dissemination of new info to a subset of the spanning tree to learn where the leaks are. By sacrificing a few sites the manager of the spanning tree learns where the leaks are. New leaks will arise in proportion to the rate of flow of people along the ideological spectrum.
The ‘other parties’ that operate these proxies are themselves privy to the traffic they carry. They are in a position to quickly discard such information so that even forcible confiscation of the hardware reveals little. The evasion technologies in development are open and available to parties of all political positions. The proxy platform is vulnerable to silent hostile intrusions depending on the security properties of the platform. The evaluation the security of such platforms and proxies is a daunting task requiring considerable technical resources or a trusted network of organizations that includes such resources.