Electrochemical dehydrogenative α-vinylation of cyclic β-ketoesters using 1,1-disubstituted alkenes is reported, producing a diverse range of α-vinyl cycloketones in good yields under oxidant-free conditions. When allylsilanes are used as alkene components, the reaction proceeds through a dual dehydrogenative and desilylative pathway, resulting in the formation of α-allyl cycloketones with good efficiency. This electrochemical strategy provides a unified approach for constructing all-carbon quaternary centers via two distinct α-functionalization processes.