This study investigated the preliminary psychometric properties of the Pathway to Independence Inventory (P2I), a transition assessment tool designed to meet the needs of transition-age students with disabilities (SWD) with support needs in the areas of adaptive skills, executive functions, and social skills. Analyses examined the item-total correlations (ITC), factor structure, internal consistency, and concurrent validity evidence of the instrument and group differences based on gender identity, age, geographic location, and disability status. Results of the ITC and exploratory factor analysis (EFA) supported dimension reduction of items that did not discriminate well, resulting in separate versions of the instrument for students and informants. Results also indicated evidence of internal consistency, limited concurrent validity evidence for the informant version, and differences in mean scores based on gender identity and age for the informant report version and on disability status for both versions. Implications for both research and practice are discussed.