"jailbreak energy" means: The unmistakable vibe someone gives off when they're in full rule-questioning, system-subverting, authority-ignoring mode — whether they're.... This is a fairly neutral word with no inherent risk attached. There is no real cause for parental concern; it is descriptive vocabulary rather than something dangerous. If your child uses it, context will usually make the meaning clear. A brief, curious question about where they heard it is generally enough to know whether to follow up.