An efficient and rapid protocol for the oxidative halogenation of tryptamines with 10% aqueous NaClO has been developed. This reaction is featured by its operational simplicity, metal‐free conditions, no purification, and high yield. Notably, the resulting key intermediates are suitable for further functionalization with various nucleophiles, including amines, N‐aromatic heterocycles, indoles and phenols. The overall transformation exhibits broad functional‐group tolerance and is applicable to the late‐stage functionalization of complex biorelevant molecules.