Substance use, sexual behavior, and reincarceration among 89 men from 5 state prisons across the USA, aged 18-29 years, were examined in relation to individual patterns of coping with community reintegration after their release from prison. Analyses of a series of qualitative interviews conducted over a 6-month period post-release revealed three global reintegration coping patterns: moving toward successful reintegration, resuming behavioral patterns that preceded incarceration, and reintegrating through withdrawal or isolation. Four key contextual factors that differentiated these three coping patterns were the consistency and extensiveness of social relationships, the nature of social support, and the degree of structural stability (e.g., stable employment and housing). Participants were assigned a Likert scale score (1 for poor rating to 3 for better rating) for their pattern of global reintegration and for their rating on each of the four contextual factors across the longitudinal qualitative interviews. Collectively, these five factors differentiated the prevalence and frequency of substance use, patterns of sexual behavior, and incidence of reincarceration as assessed by a quantitative survey administered 6 months post-release. Poorer ratings on all five contextual indices were related to the use of substances other than marijuana and alcohol. Men with less consistent social relationships reported more sexual partners. However, vaginal or anal sex without a condom was associated with greater social consistency and greater structural stability, possibly due to the presence of a steady main partner. Reincarceration was significantly associated with poorer global reintegration ratings, more negative social support, and less structural stability. These findings highlight the need to consider the role of social and structural support systems in HIV and sexually transmitted infection risk reduction interventions for men after their release from prison.