Although many adolescent risk assessment tools include an emphasis on dynamic factors, little research has examined the extent to which these tools are capable of measuring change. In this article, we outline a framework to evaluate a tool’s capacity to measure change. This framework includes: (1) measurement error and reliable change, and (2) sensitivity (i.e., internal, external, and relative sensitivity). We then used this framework to evaluate the Structured Assessment of Violence Risk in Youth (SAVRY) and Youth Level of Service/Case Management Inventory (YLS/CMI). Research assistants conducted 509 risk assessments with 146 adolescents on probation (101 male, 45 female), who were assessed every 3 months over a 1-year period. Internal sensitivity was partially supported, as a modest proportion of youth showed changes over time. External sensitivity (i.e., the association between change scores and reoffending) was also partially supported. In particular, 22% of the associations between change scores and any and violent reoffending were significant at a 6-month follow-up. However, only one change score (i.e., Peer Associations) remained significant after the Bonferroni correction was applied. Finally, relative sensitivity was not supported, as the SAVRY and YLS/CMI was not more dynamic than the Psychopathy Checklist: Youth Version (PCL:YV). Specifically, the 1-year rank-order stability coefficients for the SAVRY, YLS/CMI, and PCL:YV Total Scores were .78, .75, and .76, respectively. Although the SAVRY and YLS/CMI hold promise, further efforts may help to enhance sensitivity to short-term changes in risk.