Individualized risk assessments during HIV testing are an integral component of prevention counseling, a currently recommended behavioral intervention for patients in high-risk settings. Additionally, aggregate risk assessment data are the source of aggregate behavioral statistics that inform prevention programs and allocation of resources. Consequently, inaccurate or incomplete risk behavior disclosure during test counseling may impact the efficacy of the counseling intervention, as well as bias aggregate behavioral statistics. To quantify client-reported accuracy during the risk assessment and identify barriers and facilitators to risk behavior disclosure, we interviewed young men accessing HIV testing services in a southeastern United States city using mixed methodology. Data were collected from August 2007 to April 2008. Based on data collected via an audio and computer-assisted self-interview (n = 203), over 30% of men reported that they were not accurate during the risk assessment. Participants reported numerous interpersonal facilitators to complete disclosure. During qualitative interviews (n = 25), participants revealed that many did not understand the purpose of the risk assessment. Findings suggest that risk assessments completed during HIV test counseling may be incomplete. Modifications to the risk assessment process, including better explaining the role of the risk assessment in prevention counseling, may increase the validity of the data.