Abstract: There is a paucity of literature focusing on the challenges involved in undertaking qualitative research with convicted sexual offenders. This article will address the challenges faced by the researchers whilst conducting fieldwork with convicted sexual offenders in the prison environment and how they overcame them. Such obstacles included the recruitment of participants, informed consent, establishing researcher-participant rapport, avoiding collusion and ensuring confidentiality and anonymity. This article further reflects on the social, political and ethical-legal dilemmas, as well as the emotional aspects (both for the researcher and participant) of researching such populations. Although the focus here is on researching sexual offenders in prison, the experiences will no doubt have resonance for those undertaking research with other vulnerable populations.