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Introduction. Adverse childhood events (ACE) can lead to numerous health risks in adulthood. ACEs coupled with increased risk-taking behaviors can lead to increased risk for HIV infection, particularly in vulnerable populations. The purpose of this study was to determine if mental health symptom severity mediates the relationship between childhood household dysfunction and adult HIV risk among a group of probationers. Methods. T-tests were used to evaluate associations between demographic characteristics and cumulative engagement in sexual risk behaviors in 282 drug-involved probationers. A mediation analysis was conducted to determine the direct and indirect effect of cumulative household dysfunction and high-risk sexual behaviors through mental health symptom severity. Results. We found significant differences in the occurrence of different childhood household dysfunction problems by probationer gender, race, and criminal risk level. Mental health symptom severity demonstrated a significant indirect mediation effect of household dysfunction adverse events and engagement in sexual risky behaviors, b = .03, 95% BCa CI [.007, .057]. Conclusions. Given the high prevalence of childhood trauma in probationers and the direct associations with mental illness and sexual risk-taking behaviors, the need for offenders to have access to and receive mental health treatment while under community supervision is evident. Mental health and substance abuse treatment services can not only reduce risks for recidivism but also HIV infection and transmission within this population.