In summary, we introduce hydroxyaryl substituents as directing groups, enabling the development of bioorthogonal Tz scissors for efficient click-to-release with unprecedented reaction kinetics. Furthermore, our findings pave the way to the design of new molecular tools via incorporation of functionalities beyond aryl-OH groups, aiming to achieve intramolecular control of post-click reaction mechanisms. We are currently exploring several such strategies to ultimately advance bioorthogonal Tz/TCO bondcleavage to the next level.