This article analyzes how the Obama administration used executive power to grant waivers from federal education policies and assesses whether they used this power differently than previous administrations and in other sectors (e.g., health or welfare). The executive use of waivers to shape state policy is not a new trend. However, we find that recent education waivers differ in purpose and specificity from past education waivers, as well as waivers in other social policy arenas, and that the Obama administration is using this executive power to further its policy objectives in ways that often circumvent congressional intent. As the executive branch continues to utilize waivers as a policy lever, this research has important implications for the future of federal involvement in educational policy and provides critical background for Congress’s reaction to waivers in the recently reauthorized Elementary and Secondary Education Act.