States increasingly lean on charter organizations to take responsibility for their most underperforming turnaround schools. These efforts employ a different constellation of regulation, market forces, and community involvement that constitute more complex environments for charters. This article relates the experience of operators within the Tennessee Achievement School District adapting to stringent performance demands, weak markets, and a vocal community. Results show the pressures this environment placed on operators to improve outcomes with restricted controls while simultaneously acting as community organizations dedicated to a wide range of goals. We conclude that while charter organizations can support school turnaround, the demands of a contested and complex environment require well-resourced organizations capable of meeting diverse expectations from varying stakeholders.