Childhood maltreatment and interpersonal trauma experience is an important factor underpinning the apparent perpetuation of the cycle of social disadvantage experienced by homeless adults. This paper aimed to examine longitudinal patterns of psychological distress in a sample of 1,504 socially disadvantaged adult participants from the Journeys Home Study in Australia. The current paper utilized the “conservation of resources” theory and the concept of “risk factor caravans” to investigate the nature and implications of childhood trauma in the context of homelessness. Growth mixture modeling revealed four distinct trajectories of psychological distress as measured by the Kessler 6 across six time points (covering a period of 2.5 years): chronic, escalating, attenuating, and resistant. Our results also indicated that experiences of different types of trauma during childhood were associated with these psychological distress trajectories. In particular, adults experiencing chronic psychological distress were significantly more likely than those exhibiting distress resistance to have experienced multiple and varied childhood maltreatment, adjusted odds ratio (AOR) = 3.30, 95% CI [0.37, 6.05], p =.002. Furthermore, adult experiences of assault were found to be associated with psychological distress. These findings have important implications for mental health, as well as interventions aimed at breaking the cycle of urban poverty. Specific focus on interpersonal trauma vulnerabilities is important. Prioritizing socioecological stability, with mental health needs assessed on an individual level, may be most appropriate. This work also highlights the need to direct future attention to barriers to access and facilitation of social support services.