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Social impact bonds, known as pay‐for‐success (PFS) initiatives in the United States, have attracted attention as a novel strategy for financing and providing preventive services to the most vulnerable populations. This article provides an exploratory qualitative analysis of the Preschool PFS Feasibility Pilot grant applications and projects initiated by the U.S. Department of Education to encourage state and local exploration of PFS for implementing high‐quality preschool programs. Drawing on the public administration evidence base that informs PFS design, the authors examine the feasibility pilots’ features and investigate why grant applicants saw PFS as a promising strategy for achieving their preschool program goals. The challenges encountered, lessons learned, and perceived viability of fully executed PFS preschool programs are also discussed. Findings show that few projects are advancing toward formal PFS arrangements, with many struggling to overcome constrained capacities, structural and political barriers, and inherent incentives to minimize risk and loss...