By accounting for the perspectives of gang members, qualitative studies in Central and South America have challenged the heavy reliance on secondary material that characterizes literature in the region, including moralized preconceptions of gangs. This chapter acknowledges this important contribution but argues that qualitative gang researchers must be more attuned to methodological reflections on their positionality, particularly how their gendered status informs every aspect of the research process and requires grappling consciously with gendered power relations. How researchers navigate gender dynamics influences the narratives shared by their interlocutors, as well as their research outcomes and the way they present their results. Drawing on insights gleaned from our respective studies on gangs in Central America, the chapter contends that failure to engage with questions of positionality will only reify the marginalization of women’s perspectives, the privileging of a male gaze, and the reinforcement of gender stereotypes on gangs.