Veterans of Operation Enduring Freedom, Operation Iraqi Freedom, and Operation New Dawn enrolled in postsecondary education may experience disabilities that impact their successful participation in the academic environment. Accommodations are made available to college students with disabilities to provide opportunities for success in this environment, but in order to receive these accommodations it is essential that the student discloses their disability and informs the institution of their needs. Therefore, it is critical to understand the self-advocacy skills of student veterans with disabilities as a factor that may influence their academic success. The Student Veteran Self-Advocacy Skills Assessment (SV-SASA) is an assessment of self-advocacy skills among student veterans with disabilities. Regression analysis was conducted on a sample of 49 participants in a supported education program for student veterans with disabilities to investigate factors that explain their self-advocacy skills and academic performance, and to evaluate the psychometric properties of the SV-SASA. Results indicated that first-generation status, extent of exposure to a supported education program for student veterans, number of credits attempted, and number of self-reported health conditions explain the self-advocacy skills of student veterans with disabilities. Results also indicated that student veterans with greater self-advocacy skills achieved a higher grade point average. The SV-SASA demonstrated adequate psychometric properties as an assessment of self-advocacy skills in the sample. Implications for service providers in the postsecondary education setting working with this population and suggestions for future research are discussed.