How hollow government can go is a long-standing question that has not been fully answered. In particular, the literature has highlighted the importance of contracting monitoring, but has rarely examined whether or when this function can be successfully outsourced. Extending and integrating theoretic approaches that are relevant to government contracting, this article proposes six conditions that public managers must address in order to successfully outsource the contracting oversight function. The framework is then applied to the case of Florida’s experiment with contracting out financial and programmatic monitoring of outsourced child welfare services. The discontinued experiment in Florida illustrates the challenges that arise when outsourcing the contracting monitoring function in a politically charged environment.