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Adolescents often engage in behaviors such as substance use and risky sexual activity that can lead to negative health and psychological consequences for themselves and others. Accurate measurement of these behaviors in surveys is challenging given that the behaviors are often viewed as undesirable and/or are illegal, so it is important to test the psychometric properties of instruments used to assess adolescent risk behaviors. The current study aimed to assess the test-retest reliability of a widely used measure of youth risk-taking behavior, the Youth Risk Behavior Survey (YRBS). A sample of 156 at-risk adolescents aged 16–18 years (81% male; 61% White) completed the YRBS retrospectively across intervals ranging from 3 to 12 days during their stay in a residential program at which they were under close supervision and had limited ability to engage in new risk behaviors. Participants were asked to complete the YRBS based on their "typical" (pre-program) behavior at both administrations, which were 10–14 weeks into their stay. The reliability of responses was assessed using kappa and weighted kappa analyses. Findings indicate moderate to substantial reliability for nearly all items, suggesting that at-risk youth reliably reported their engagement in health risk behaviors across multiple administrations and supporting the psychometric strength of the YRBS measure for use with this population. [ABSTRACT FROM AUTHOR]