This study examines how the re-entry process is related to structural barriers in the community and to motives for engaging in illegal behavior—two key risk factors for recidivism. We analyzed survey data collected on perceptions of community re-entry, employment opportunities, neighborhood violence, and illegal behavior motives from 379 formerly incarcerated and street-identified Black-American community members residing in Wilmington, Delaware (Mage = 32.3/8.9 years old; 77.0% men; 100% Black) by employing Street Participatory Action Research (Street PAR) methodology. We found that negative perceptions of re-entry correlated positively with (i) hardship caused by structural barriers in the community, specifically blocked employment opportunities and neighborhood violence, and (ii) motives for engaging in illegal behavior. Notably, the link between negative perceptions of re-entry and motives for illegal behavior became significantly weaker when the influence of structural barriers on these individual-level factors was included in a multivariate model. Results suggest negative views of the re-entry process reflect the resource-scarce and stressful environments people are living in, and structural barriers can account for the relationship between negative re-entry experiences and why individuals are motivated to engage in illegal behavior. Findings underscore the importance of improving the economic conditions of communities with high numbers of returning citizens.