Bioorthogonal bond‐cleavage reactions have emerged as a powerful tool for precise spatiotemporal control of (bio)molecular function in the biological context. Among these chemistries, the tetrazine‐triggered elimination of cleavable trans‐cyclooctenes (click‐to‐release) stands out due to high reaction rates, versatility, and selectivity. Despite an increasing understanding of the underlying mechanisms, application of this reaction remains limited by the cumulative performance trade‐offs (i.e., click kinetics, release kinetics, release yield) of existing tools. Efficient release has been restricted to tetrazine scaffolds with comparatively low click reactivity, while highly reactive aryl‐tetrazines give only minimal release. By introducing hydroxyl groups onto phenyl‐ and pyridyl‐tetrazine scaffolds, we have developed a new class of ‘bioorthogonal scissors’ with unique chemical performance. We demonstrate that hydroxyaryl‐tetrazines achieve near‐quantitative release upon accelerated click reaction with cleavable trans‐cyclooctenes, as exemplified by click‐triggered activation of a caged prodrug, intramitochondrial cleavage of a fluorogenic probe (turn‐on) in live cells, and rapid intracellular bioorthogonal disassembly (turn‐off) of a ligand‐dye conjugate.