"fail safe technological solution" = tor? Grug, that's not good advice to give out.
First, it's never good to rely on anything. Second, it's well known that people run tor gateways as a means to acquire 'interesting' traffic, and that probably includes law enforcement (though Applebaum does seem to have an honest aura, the project did originate from US government funding). Many people relying on tor probably do not realise this.
I believe the term Grugq used was "fail-closed" (at least that's what he said rather than wrote). By that, he didn't mean that Tor was foolproof, but rather that you should use a setup that sends information through Tor by default (opt-out), rather than using something where you have to activate it in order to use it (opt-in). The idea is to reduce the potential for silly mistakes like engaging in activities with Tor off by accident.
Also, one of the questions he answered at the end of the talk was about whether Tor could protect you against determined state actors, and he talked about a certain flaw where if you have control over a certain percentage of the Tor network you could infer people's source IPs. He also speculated on what levels of government Tor would or would not be a viable means of protection against, so I think he'd agree with you about the risks of Tor.
First, it's never good to rely on anything. Second, it's well known that people run tor gateways as a means to acquire 'interesting' traffic, and that probably includes law enforcement (though Applebaum does seem to have an honest aura, the project did originate from US government funding). Many people relying on tor probably do not realise this.
Be careful out there!