This article focuses on five aspects of data collection that were effective for successfully engaging and retaining 11 vulnerable youth in a short-term longitudinal qualitative study of school and work transitions. Each youth in this study attended five meetings with the researcher over the course of three to four months, and there was no attrition. The five strategies discussed are: (1) use of self and researcher role; (2) screening procedures; (3) initial interview; (4) structure and process of participant stipends; and (5) frequency of contact. The article also reviews selected literature on retention of participants in longitudinal studies and highlights areas in which further research on engagement and retention is needed.