When students drop out of high school there are substantial social and economic consequences that can persist throughout their lives. They are more likely to be unemployed, to become teenage parents, to become involved in the criminal justice system, and to suffer a lifetime of low wages. Dropout rates soared during the COVID-19 pandemic as schools struggled to adapt and keep students engaged. During the 2021-2022 school year, Communities In Schools® (CIS®) introduced the Reengagement Coordinator (RC) Initiative, with the goal of reengaging high school students (particularly eleventh and twelfth grade students) who did not reenroll in school or were chronically absent. CIS partnered with MDRC in 2021 to conduct a qualitative evaluation of the implementation of the RC Initiative. The evaluation set out to answer key questions related to the reasons for students' disengagement, how RCs identified students, which strategies were most effective, and the potential pathways for reengagement. This brief summarizes the main findings and shares takeaways and considerations for practitioners in schools and other organizations who are looking to work with and reengage disengaged students or create a dedicated position to reengage students. [This research project received funding from Blue Meridian Partners.]