Compared to their non-homeless peers, chronically homeless adults are much more likely to have a history of incarceration. In turn, homelessness is associated with increased morbidity, lack of access to adequate healthcare services, and decreased life expectancy. This study investigates whether age at first incarceration is associated with age at first homeless experience and with lifetime duration of literal homelessness. Study participants are homeless adults entering permanent supportive housing (PSH) in Los Angeles County, California, that have experienced incarceration prior to their first experience of homelessness (n = 230). Multivariate linear regressions were conducted to determine association between age at first incarceration with: 1) age at first literal homelessness and 2) lifetime duration of literal homelessness. Results indicate that incarceration as a juvenile, and young adult is significantly associated with earlier literal homelessness experiences and may be associated with longer durations of literal homelessness, for adults entering PSH. Moreover, women incarcerated as juveniles and entering PSH first experienced literal homelessness earlier than comparable men. Our findings suggest the need for long-term supportive services for persons incarcerated before 25 years old, especially for women. Moreover, these findings refine the working knowledge that prior incarceration increases risk for prolonged homelessness and can help agencies complete more accurate risk assessments.