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Longitudinal research designs enable us to make detailed observations about psychological and sociological processes and examine how these mechanisms vary over time. Participant retention is a major challenge to longitudinal designs. Research has shown that collecting multiple sources of contact information (i.e., phone number, email, physical address) and asking participants for secondary party information can significantly improve retention rates in longitudinal studies (Western, 2018). Despite these strategies, a number of unanticipated challenges arise, and these may impact participant retention in a significant manner. The current research highlights the main challenges associated with participant retention in the first year of a three-year longitudinal follow-up of approximately 400 recently released individuals on parole in New York City. This study outlines the major reasons for participant attrition, potential solutions, ongoing barriers to retention, and the unique challenges of participant attrition in the context of New York City. The presentation addresses the implications of the findings for future longitudinal research with justice-involved populations, particularly studies conducted in urban areas.