Contrary to decentralization trends, recent policy recommendations suggest stronger regulations for educational public-private partnerships to improve quality for disadvantaged populations. We conducted a comparative analysis of the implementation of recentralized regulations for contracted schools in two Colombian subnational jurisdictions with different outcomes. Our findings indicate that a high dependency between local government and contracted schools to increase enrollment and secure schools’ financial stability leads to collusion between these actors against centralized regulations. By contrast, a lower dependency favours the alignment of goals between national and local governments, which improves selection and monitoring of contracted schools. This second scenario, however, requires high local capacity and considerable public-school supply—two conditions ignored by the theoretical propositions that support recentralized regulations. Our conclusions discuss the limitations of market regulation approaches to fix problems of contracted schools, and the dilemmas of improving quality of public-private partnerships in contexts of weak governance and conflicting pressures.