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Scholars have devoted a significant amount of attention to the difficulties in accessing vulnerable populations for the purpose of conducting qualitative research. I explore the merits and challenges specifically of conducting *comparative* research on vulnerable populations. Drawing on an ongoing study on incarceration, homelessness, and masculinity, I discuss the intricacies and difficulties of conducting research on two very different, but also very vulnerable, populations that are generally considered ‘deviant’: incarcerated and homeless men. I consider some misperceptions that researchers may have about the implications of varying levels of gate keeping when accessing different vulnerable populations. I further argue that despite the challenges inherent in studying populations that are considered both deviant and vulnerable, social scientists should not shy away from accessing and conducting comparative research on these populations.