Herein, we disclosed a sustainable electrochemical approach for site-selective C–H mono and bis-chalcogenation (sulfenylation or selenylation) of indolizine frameworks. Diversely functionalized disulfides and diselenides possessing EDGs and EWGs were successfully reacted with a variety of indolizines to directly access sulfenylated/selenylated indolizines in 40–96% yields. A mechanistic radical pathway was also validated with control experiments and cyclic voltammogram data.