Charter schools and special education for disabled students are based on conflicting education reforms and agency oversight principles. Charter schools operate in a culture of regulatory freedom and flexibility. They arose out of the modern era of accountability reform, in which student outcomes are the primary measure of school success and the driving engine of agency oversight. In stark contrast, special education laws were conceived in the civil rights era of education reform, which emphasized process and paid little attention to outcomes. The education of disabled students is steeped in a culture of regulatory oversight focused on rigid compliance with complex procedures. Special education and charter schools stand on competing foundations in the same schoolhouse. The Article discusses this culture clash and the consequences to disabled students. The uncomfortable fit between charter schools and special education often leads to violations of disabled students’ civil rights. The Article suggests how the three primary sources of law affecting charter schools—federal law, state law, and charter agreements—should be changed to achieve a seamless fit of charter schools’ square peg into special education’s round hole for the benefit of disabled students.