In Latin America and the Caribbean, more students than ever are entering secondary school — but too many of them never complete this level and successfully graduate. While over 90 percent of children in the region now transition from primary to lower secondary school, only 59 percent complete upper secondary school (UNESCO, 2017). In school, many students are often unsupported, do not learn, and do not see how their education will prepare them for the future. Outside of school, teen pregnancy and poverty continue to be significant hurdles. These obstacles, which together push and pull students out of school, have enormous implications: youth who do not complete secondary school earn lower incomes, face lower rates of employment, and are more likely to use drugs or be engaged in criminal activity. More broadly, these challenges mean that countries in the region struggle to build productive workforces with the skills necessary to generate economic growth in the 21st century. Case studies of four promising initiatives in Mexico and Chile explore strategies to identify at-risk youth, support school leaders and teachers, and foster students’ socioemotional skills. Based on these insights, we offer recommendations for decision-makers throughout the region to consider when designing and implementing strong and coherent school retention strategies. Incorporating a gender perspective when designing interventions, improving coordination between complementary school-related initiatives, and building strong early warning systems are some of the recommendations that emerged from our case studies in Chile and Mexico, which are applicable elsewhere in the region.