Executive leadership of the U.S. Department of Education (USDOE) initiated a flexibility offering from No Child Left Behind. Our work explores specific design decisions made in these state-specific accountability systems as associated with state political environments, resources, and demographic characteristics. Our analysis, focused on 42 states with approved flexibility waivers, provides some evidence that design decisions are associated with prior education policies, political leanings, and financial resources within each state. Policymakers should also take note, as these results suggest that state political factors may influence how state policymakers will react in future negotiations with the USDOE.