A modular and practical approach has been developed for the stereoselective formation of elaborate allylic alcohols through a three-component reaction (3CR) between vinyl cyclic carbonates, olefins, and various radical precursors using dual photoredox/Ni catalysis. The developed process expands the potential of radical-based allylic alkylation to multicomponent approaches under high regio- and stereocontrol with ample variation of the individual reagents and offers access to compounds featuring sterically congested and functionalized quaternary carbon centers. The catalytic protocol can be expanded to other allylic precursors, and the stereoselectivity is reversed by simply changing the photocatalyst.