Research has found that teachers of color contribute to better academic, behavioral, and socioemotional outcomes for diverse students. Despite these benefits, the diversity of the teacher workforce in the United States has not kept pace with increases in student diversity. States have adopted aspirational legislation aimed at increasing teaching diversity, but have fallen short of diversity targets. This qualitative study examines barriers to increasing teacher diversity by presenting the efforts to do so at 28 diverse-by-design charter schools across five locales. Despite a range of approaches, these schools struggled to meet teacher diversity targets, suggesting a need for states to adopt alternate policy instruments rather than relying on legislative mandates.