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There is a paucity of literature focusing on the challenges involved in undertaking qualitative research with convicted female sex offenders. This paper seeks to examine the challenges faced by a researcher while conducting fieldwork with convicted female sex offenders in the communities in which they reside. Major challenges that will be addressed in the paper include: the recruitment of participants, balancing IRB and respondent expectations regarding informed consent, establishing researcher-participant rapport, avoiding collusion and ensuring confidentiality and anonymity. This article further reflects on the social, political, and ethical dilemmas, as well as the emotional aspects (for both researcher and participant) of researching such populations. Although the focus here is on researching female sex offenders, the experiences will likely be applicable for those undertaking research with other vulnerable populations.