Through work on the Pathways through Medicaid to Prevention project—the environmental scan, discussions with state and federal Medicaid experts, and calls with collaborators—a number of factors were identified that affect the successful implementation of prevention strategies financed through Medicaid. We identified those factors as accelerators that facilitate innovative strategies, barriers to innovation and transformation, and conditions for success that are critical for a state to have in place as it begins transforming its health care delivery system to include a population health focus.