A new AB(2) monomer was synthesized for use in the preparation of a hyperbranched poly(aryl ether oxadiazole) with terminal phenol functionality. The AB2 monomer contains two phenolic groups and a single aryl fluoride group that is activated toward nucleophilic displacement by the attached oxadiazole ring. The nucleophilic substitution of the fluoride with the phenolate groups led to the formation of an ether linkage. Subsequently, a hyperbranched poly(aryl ether oxadiazole) having approximately a 44% degree of branching, as determined by a combination of model compound studies and H-1 NMR, was obtained. The terminal phenolic groups underwent facile functionalization, furnishing hyperbranched polymers with a variety of functional chain ends. The nature of the chain-end groups had a significant influence on the physical properties of the polymers, such as the glass-transition temperature and their solubility.