Trifluoromethyl containing heterocycles are an integral part of many biologically active compounds in the agro and pharmaceutical chemistry. Herein, we report an efficient and concise three-step synthesis of 5-halo-6-trifluoromethylpyridine-3-carbonitriles from a trifluoroacetyl vinylogous enamine starting material. Hydrolysis furnishes the carboxylic acids.