While the number of young people entering the formal criminal justice system has fallen steadily in recent years, youth reoffending rates have continued to increase and currently stands at 42% (Youth Justice Board, 2017). My doctoral research explored the complex factors and processes involved in desistance (stopping offending), looking closely at the quality of the relationship between young people and youth justice practitioners. Empirical research was conducted and the principal qualitative design used was a single exploratory case study, based in two geographical areas. The research used both interviews with a small group of young people known to local Youth Offending Teams, and focus groups with youth justice practitioners. Transcripts were analyzed using Yin’s approach, with the aim of identifying links between multiple factors, allowing the study to look at youth offending in context. The findings of my doctoral research could be used to inform youth offending policy and practice, adhering to the Welsh government’s vision and commitment to prevent young people entering the criminal justice system in the first place and to reduce reoffending in Wales. This case will take the reader through the processes involved in conducting a research project, offering an informative, interesting, and transparent view of the challenges that researchers can face when conducting qualitative research using vulnerable participants.