This article examines collaboration between Head Start and the Virginia Preschool Initiative to see how collaborative challenges vary given the degree of collaborative activity between programs. Limited collaborative management research addresses how challenges can change with varying degrees of collaborative activity; this research addresses the gap. Collaborative challenges are discussed through a series of three paradoxes, with evidence of three degrees of collaborative activity: cooperation, coordination, and collaboration. Drawing on qualitative interviews, the author reports that challenges differ with varying degrees of collaborative activity and that coordination between programs produces the most challenges.