Chain drug stores have increased their health care role through expanded pharmacy services and retail health clinics. They also are major food retailers. This creates a tension between health promotion and sales of unhealthy foods and beverages to pharmacy customers. This article explores opportunities to improve the nutritional quality of foods sold at chain drug stores that differ from general healthy food retail approaches. It considers the legal limits on marketing to pharmacy customers; the potential roles of health insurers, pharmacy benefit managers and retail health clinics to voluntarily improve food offerings; and formal policymaking legal considerations and approaches.