As with most other serious street crimes, motor vehicle theft is a male-dominated offense. Yet, women do engage in motor vehicle theft, albeit at a reduced rate of participation. Here we examine the gendered nature of motor vehicle theft through direct comparison of qualitative data obtained from 35 juvenile and adult men and women actively involved auto theft in St. Louis, Missouri. By tracing similarities and differences between men’s and women’s pathways of initial involvement, enactment strategies, and post-theft acts, we provide a contextual analysis of offender’s perceptions and behavior. Such an approach allows a more precise discussion on gender’s influence (or lack of) on motor vehicle theft. Analysis shows that initiation into auto theft and property disposal networks are governed by male gatekeepers, and this leads to some key similarities in techniques between men and women. The ways in which women negotiate male-dominated networks is also discussed with particular emphasis on the innovative strategies they draw upon to accomplish their crimes within these landscapes and when opportunities are constrained by male gatekeepers.