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Although adequate housing has been declared a fundamental human right, millions of Americans reside in substandard living conditions. Research on housing insecurity consistently demonstrates that it produces a variety of negative physical and mental consequences, while also exacerbating difficulty in other domains, thereby functioning as a key mechanism reproducing disadvantage. This research uses data from the Violence Intervention Worker Study (VIeWS), a survey of street outreach workers in Chicago, IL. To uncover heterogeneity in how housing insecurity manifests, I use latent class analysis to identify three subgroups of workers experiencing qualitatively distinct forms of housing insecurity. I find these groups differ along key dimensions, including patterns of justice system involvement, mental health symptomology, and how the COVID pandemic affected their housing. Those experiencing the greatest housing deprivation simultaneously experience other forms of disadvantage. Furthermore, results indicate that groups differ in how they perceive their neighborhoods, and these perceptions do not align with objective conditions. These findings contribute to research on housing insecurity and cycles of disadvantage, expand our understanding of the nexus between incarceration and housing insecurity, and have practical implications regarding the need to provide support to violence interventionists experiencing housing hardship.