Considering that ISIS has a website[1] protected by TOR, I'm pretty sure they could figure out how to jail break an iPhone, which takes about 10 minutes and a YouTube tutorial.
I apologize, if I'm wrong, but I can't help but feel like you're being disingenuous.
Though there is a tor website is does it actually get visited by people? Seems like Twitter, Facebook, YouTube and Telegram has been more successful for them.