The gem-difluoroallyl group is a sought-after structural motif commonly found in pharmaceutical compounds. Despite its appeal, achieving a controlled synthesis of both α,α- and γ,γ-difluoroallylated compounds has proven to be a challenging task. This study presents a new approach to difluoroallylation, which utilizes a regiodivergent C-H bond reaction catalyzed by ruthenium catalysis. This method enables the meta and ortho C-H α,α- and ortho C-H γ,γ-difluoroallylation of arenes using 3-bromo-3,3-difluoropropenes.