This study explores the immigration-related family separation and reunification experiences of 7 Mexican and Central American families. The data collection methods included participant observation and in-depth interviews with teenagers and their mothers. The study also incorporated longitudinal data collected on participants as part of the Longitudinal Immigrant Student Adaptation study (LISA). These longitudinal data included participant observation notes, semi-structured interviews with children and their parents, and schooling outcome data. Data were synthesized to create 7 detailed case studies that bring to life the experiences of immigrant families as they manage complex reunifications during a span that averages 8 years. While reunifications posed a number of challenges for all families, many families were able to manage these events over time. For some families, however, the challenges posed by difficult reunifications were insurmountable and resulted in strained mother-child relationships and maladaptive behaviors in children. The use of case study methodology allowed the inclusion of contextual factors generally overlooked in studies on immigration-related family separations and were found to have a significant impact on how these events are experienced. The longitudinal perspective highlighted the importance of examining reunification processes over time because reunification outcomes can change over the course of time as families adjust to these events and to their host environment. Furthermore, by exploring these events both contextually and longitudinally, this study addresses existing gaps in the literature and moves beyond current frameworks.