In 2013, the Chicago Public School District passed a sexual health education policy requiring schools to provide medically-accurate, age-appropriate, National Sexuality Education Standards-aligned, comprehensive sexual health education (SHE) to K-12^th grade students; provide three forms of parental notification; and have two SHE-trained instructors. Funding from a cooperative agreement between the Centers for Disease Control and Prevention’s Division of Adolescent and School Health and CPS’s Office of Student Health and Wellness (OSHW) is being used to evaluate the implementation of this policy. In partnership with evaluators from the University of Illinois at Chicago’s School of Public Health, the following questions are being addressed: “What are the characteristics of SHE implementation in schools?” and “What are the facilitators and barriers to SHE implementation?” Twenty key informant interviews were conducted with principals and SHE teachers from schools, based on their SHE-policy compliance status, to identify classroom and school-level facilitators and barriers. Preliminary results reveal several structural factors that promote and hinder SHE implementation. Facilitators, such as training several instructors, integrating SHE in other courses, monitoring SHE implementation, and partnerships with community-based organizations for SHE instruction were identified during interviews. Barriers, such as competing educational priorities, negative parental views, and lack of knowledge of the SHE curriculum and training were revealed as well. These results are being used to provide technical assistance to schools in the district and promote SHE policy compliance. These findings can assist school districts, especially large districts, in determining the supports and resources needed for the scaling of similar policies.