Despite a rise in school principal vacancies in recent years, principals of Color are still underrepresented in many K-12 school districts across the United States. Continued racial bias remains a barrier and deterrent for aspiring principals of Color, particularly in homogenous, predominantly White school districts and communities that allow stereotype-driven selection criteria such as culture fit in hiring decisions. Principal preparation pathways can provide a vehicle for increasing diversity in school leadership, though existing practices have yet to demonstrate significant and widespread progress in existing racially homogenous communities. This conceptual work presents a theoretical model for considering, addressing, and improving the diversity of principal pathways to increase principals of Color in predominantly White school districts and communities. Discussion of the model, with suggestions for school district leaders and researchers, is included.