This study presents multiple dimensions of analyses of adolescent pregnancy and accompanying healthcare reforms in the Philippines. It also highlights the contrast between the promise of decentralized healthcare and on-ground health outcomes for complex issues such as adolescent pregnancy. It discusses the economic and humanitarian impacts of adolescent pregnancy in the Philippines and the complexity of social policy design therein. Policy options as an alternative are presented, considering four problem dimensions (substantive, behavioral, operational, and political) vis-à-vis the rules of the game: incomplete information, information asymmetry, high transaction costs, and low credible commitment.