X-ray structures of Co(III)[(CF(3))(3)Cor](PPh(3)) [(CF(3))(3)Cor = meso-tris(trifluoromethyl)corrolato] and Cu[(CF(3))(4)Por] [(CF(3))(4)Por = meso-tetrakis(trifluoromethyl)porphyrinato] revealed planar and highly ruffled macrocycle conformations, respectively, in line with analogous observations for a handful of other meso-perfluoroalkylated porphyrins and corroles reported in the literature. To gain insights into the difference in conformational behavior, we evaluated DFT (BP86-D/TZP) ruffling potentials for a variety of corrole complexes, as well as their porphyrin analogues. The calculations led us to conclude that corrole derivatives, in essence, cannot ruffle.