Considering strengths when planning for postschool outcomes is critically important for all youth, including youth with disabilities, as strengths should guide the identification of meaningful postschool goals. However, there are a limited number of strengths-based assessment tools that have been validated with youth with disabilities. This article reports the results of a pilot study of the application of the short form of the VIA Inventory of Strengths for Youth (VIA—Youth) to secondary students with and without disability labels. Although the VIA-Youth has been studied in youth without disabilities, it has not been applied to youth with disabilities. Similarities in the reliability of the scores were found across youth with and without disabilities. However, students with disabilities tended to score lower on character strengths than students without disabilities. We were unable to replicate, using confirmatory factor analysis, the theoretical structure used to develop the VIA-Youth, although youth with and without disabilities did demonstrate measurement invariance when fitting a one-factor model. Further work is needed to merge theoretical and empirical models for the factor structure of the VIA-Youth. Implications for future research and practice related to strengths-based assessment and intervention are discussed.