Traditional resources for ascertaining risk and protection for disengaged youth are often unsuitable, due to the stamina and skill required to complete them. Many of these tools assess risk without considering participants’ potential for personal growth. The present study outlines the development and initial validation of a tool titled the Contextualized Assessment Tool for Risk and Protection Management (CAT-RPM), which was administered to 499 participants across a range of high school settings. Six factors emerged that were highly correlated and had good internal consistency. Multivariate tests strongly suggest that the CAT-RPM is a valid and psychometrically sound assessment tool for differentiating groups across sex, age, and antisocial behavior. The research reveals a reliable measure of risk and protection that can assist young people to recognize and build on their strengths and adds a positive dimension to traditional risk assessment tools.