Finding and retaining a job is one of the most challenging problems women confront after being released from prison. Given the dynamic and fluid interactions between legal and illegal work, we argue that to better identify and describe job trajectories after release, we must simultaneously consider disparities in work types and offending behavior. We leverage a unique dataset - the Reintegration, Desistance and Recidivism Among Female Inmates in Chile study- to describe patterns of employment within a cohort of 207 women during the first year after being released from prison. By considering different types of work (i.e., self-employed/employed, legitimate/under- the-table) and including offending as another type of income-generating activity, we adequately account for the intersection between work and crime in a particularly understudied population and context. Our results reveal stable heterogeneity in employment trajectories by job type across respondents but limited overlap between crime and work despite the high levels of marginali-zation in the job market. We discuss the role of barriers to and preferences for certain types of jobs as possible explanations for our findings.