By merging C-C and C-F bond cleavage, we developed a regioselective ring opening/gem-difluoroallylation of cyclopropyl ketones with α-trifluoromethylstyrenes, which proceeds under the catalysis of iron with the combination of manganese and TMSCl as the reducing agents, providing a new entry to the synthesis of carbonyl-containing gem-difluoroalkenes. Remarkably, the ketyl radical-induced selective C-C bond cleavage and the following generation of more-stable carbon-centered radicals enable complete regiocontrol of this ring opening reaction for various substitution patterns of the cyclopropane ring.