Internet cigarette vendors (ICVs) advertise low prices for tobacco products, subverting public health policy efforts to curtail smoking by raising prices. Many online retailers in the United States claim affiliation with Native American tribes and share in tribal tax-free status. Sales of discounted cigarettes from both online vendors and brick-and-mortar stores have angered non-Native retailers and triggered enforcement actions by state and federal governments in the United States concerned over lost cigarette excise tax revenue. Examination of the history and politics of cigarette sales on reservations and attempts to regulate Internet cigarette sales highlights the potential role for greater use of negotiated intergovernmental agreements to address reservation-based tobacco sales. Our review notes global parallels and explicates history and politics of such regulation in the United States, and offers background for collaborative efforts to regulate tobacco sales and decrease tobacco use.