We herein report the palladium(II)-catalyzed bromination and iodination of a variety of alpha-hydrogen-containing carboxylic acid and amino acid-derived amides. These reactions are exclusively enabled by quinoline-type ligands. The halogenated products obtained in this reaction are highly versatile and rapidly undergo further diversification. Further, we report the first example of a free carboxylic acid-directed Pd(II)-catalyzed C(sp(3))-H bromination, enabled by quinoline ligands.