An unprecedented metal-free regioselective halogenation of 2H-indazoles has been revealed, which not only realized the highly selective synthesis of mono-halogenated products, but also completed poly-halogenations by fine tuning the reaction conditions. Various mono-/poly-/hetero-halogenated indazoles were obtained in moderate to excellent yields. Notably, this approach features environmentally friendly solvents, mild reaction conditions, simple execution and short reaction time.