Veterans enrolled in postsecondary education may experience service-related health conditions that undermine their success on campus. Supported education services can target student Veterans' self-advocacy skills, thereby facilitating their acquisition of academic accommodations that foster academic success. The purpose of this study was to (1) investigate change in student Veterans' self-advocacy skills and academic performance over time receiving supported education services, and (2) investigate factors that influence change in their self-advocacy skills and academic performance. We collected measures of "self-advocacy skills" (Student Veterans Self-advocacy Skills Assessment [SV-SASA]) and "academic performance" (grade point average) at six time points for 99 student Veterans enrolled in the New Start for Student Veterans (NSSV) supported education program. We used multilevel modelling to determine whether self-advocacy skills and academic performance changed over time receiving supported education services, and whether first-generation status and dosage of intervention explained change in these outcomes. We additionally investigated whether SV-SASA score influenced change in academic performance. Results indicate that student Veterans' self-advocacy skills improved over time receiving supported education services. Further, a greater dose of NSSV services was associated with greater self-advocacy skills across the semesters, irrespective of how long they received services. Student Veterans' academic performance did not change over time spent in the supported education program. We discuss the implications of findings for research and practice.