Working through a lens of administrative governance, hermeneutics, and boundary spanning, we spent 18 months studying the Ohio Children’s Trust Fund (OCTF) as it began its transition from a county to a regional funding model. Using observations and interviews of regional directors and administrative teams, we were interested in learning more about the role of boundary spanning and hermeneutics during the transition process. In other words, attempting to answer the question on what makes boundary spanning work at the level of the boundary spanner? The case study research produced four primary findings: (a) state and regional administrators desired a transitional approach that meant dispersing and distributing power and decisions to regional leaders; (b) political, time, and budget constraints worked against these desires; (c) boundary spanning efforts failed to produce a resource network; and (d) seeking understanding between the macro deterministic goals of the state to the micro regional and local needs produced an exercise in philosophical hermeneutics—particularly at the boundaries of the region and the state, as actors interpreted what they saw, read, and thought. We concluded that public administrators might better cope with the uncertainties associated with program transitions by more fully developing a hermeneutic mind-set for exploratory bias over confirmatory bias when engaging in boundary spanning and forming collaborative networks.