While I broadly agree with Shirky that free communication between people in authoritarian societies is a more important driver of social change than communication with the outside world, we have to recognise that the two can't be neatly separated. One of the reasons people currently use circumvention tools is to reach social media sites where they can communicate with other people who are behind the same firewall. That's a crazy situation for two reasons.
First, it turns commercial entities like Facebook, which couldn't give a fuck about fighting censorship, into vital tools for opposition movements. If there's one thing the WikiLeaks/Anonymous bunfight has shown, it's that internet companies aren't mature enough as institutions to balance their short term political and financial interests against their long term responsibility to protect free speech. We can't rely on them.
Second, it means that all communication between people in authoritarian societies has to cross the border twice, even though borders are among the easiest places to monitor and control. If you wanted to design a communication system for prisoners in neighbouring cells, I doubt your design sketch would begin, "First get the message to a trusted third party outside the prison."
Unfortunately, moving the social media sites inside the firewall doesn't solve the problem. Take China for example. There are already Chinese equivalents of Facebook, Twitter, and other firewalled sites, but they're subject to a variety of pressures to police their users, especially those that start to form political groups. If Facebook isn't going to stand up for Chinese dissidents then Baidu certainly won't.
It's also pretty tough to maintain social media sites outside the firewall that are dedicated to supporting opposition movements - such sites are susceptible to DDoS attacks and subtler forms of infiltration and monitoring, as in the Ghostnet case. The basic problem is that the web wasn't designed or implemented with censorship-resistance in mind. Let's not ask anyone to bet their life on the security of Wordpress.
So what do we do? In my opinion we need new tools. Tools that are designed with security in mind, that don't rely on servers inside or outside the firewall, that can be used from an internet cafe or a mobile phone, that don't produce easily recognised traffic patterns, that can be used to hold meetings, plan rallies, or just tell jokes - in short, to talk to people you trust without revealing anything to people you don't. We already have some partial solutions we can learn from - Freenet, WASTE, txtmob, CryptoSMS, Gazzera, Retroshare, SocialVPN - and a million research papers that never made it as far as implementation. Now we need some specs, some code, many eyes and regular backups. :-)