This research investigates the relation between directors’ and officers’ insurance (hereafter, D&O insurance) and managerial ability. Using data from the Taiwan capital markets from 2011 to 2017, we find that D&O insurance increases managerial ability and show that the effect of D&O insurance on managerial ability is more prevalent when a firm is in the following situations: 1) CEO is in the early stage of tenure, 2) the firm belongs to a family-controlled group, and 3) the firm has higher environmental uncertainty. Finally, our study shows that D&O insurance strengthens the relation between managerial ability and firm performance.