Rural school districts must comply with the rules set forth through federal legislation such as No Child Left Behind (NCLB) in exchange for their share of federal education funds. In general, research shows that when policy is conceived, it is framed with urban school districts in mind; rural schools must apply rules designed for urban schools onto their rural contexts. This qualitative case study analysis of two rural school districts aims to demonstrate how seemingly general policies complicate educational practices in rural schools. The research questions attempt to address the consequences of one-size-fits-all educational policies imposed in rural Title I schools. This study identifies the sources of conflict that emerge as rural school districts attempt to comply with the provisions of NCLB. Related to the sources of conflict, this study identifies how specific factors, either in the design of the education policy or in local context and circumstances, hinder compliance with NCLB. This comparative case study analyzes interviews, NCLB monitoring documents, and artifacts from each community to understand the context in which rural schools operate. A comparison and analysis of the case studies determined that 1) burdens on rural schools can be reduced through modification of policies when the context of rural schools is taken into account during the policy design phase, 2) local contexts and local leadership capacity determine the success or failure of policy, and 3) federal dollars can be leveraged to improve local initiatives. This study adds nuance to the critique of "one-size-fits-all" policies applied onto different local settings and examines how rural schools maintain compliance with the federal regulations.