This qualitative research project aims to close the gap created by our country’s physical distance to many newcomers’ countries of origin as well as by our likely unfamiliarity with others’ experiences due to cultural and language barriers. Drawing from conversations with 10 participants involved in education, ethnographic research, and refugee resettlement, four main findings were identified that serve to explain how Sullivan High School functions within the larger CPS system. Participants’ personal sentiments offered explicit relationship-building strategies that prioritize trust, revealed a shared commitment to open-minded teaching and learning, recognized the value of newcomer students on a larger scale, and highlighted the important role external organizations play in students’ lives. Overall, this research finds the need for a willingness to reevaluate current operations and duplicate models that have demonstrated success, adoption of personalized learning in pursuit of holistic evaluation of students, and increased transparency and communication at all levels of operation. Implementation of these three policy recommendations could enable schools to pursue greater goals for their students, which ultimately benefits communities at large.