Many widely publicized arrangements bearing the popular “public–private partnership” label are complex, long-term contracts between municipalities and private companies. In theory, these innovative contracts offer substantial public benefits, including improved service quality, risk sharing with the private sector, and cost savings. In practice, however, the challenges that long-term contracts pose can undermine their successful implementation at the local level. Drawing on illustrative cases, this article explores some practical impediments to achieving market-driven competition, equitable risk sharing, effective performance guarantees, and appropriate transparency in innovative long-term contracts. It examines the inapplicability of the partnership model to most commercial transactions between government and business, the risks of uncontrollable circumstances, the impact of local resource constraints, and barriers to transparency in long-term contracts. It concludes that local governments embarking on long-term contracts must invest in specialized expertise, effective contract management, and strong governance structures.