Four-membered rings are common in pharmaceuticals and bioactive natural products due to their ability to improve both potency and metabolic stability. Herein, we report a subtle strain-release-driven aroylation of four-membered Michael acceptors via decarboxylative Giese reactions that occur under visible-light photoredox catalysis. Our methodology leverages α-oxo acids as acylating agents and uses strain release to overcome steric challenges that traditionally hinder addition to β,β-disubstituted Michael acceptors. The nature of strain release radical addition to strained rings further offers a unique framework for the synthesis of complex molecules with potential applications in drug discovery and medicinal chemistry.