Effective veteran-student programs that include advising help to bridge military culture with campus culture. These programs assist with military-to-campus transitions and achieving veteran-student academic success. Persistent outreach is an advising strategy that includes proactive and intentional engagement that anticipates student concerns. The records of 448 veteran-students eligible for the Veteran Student Support Services (VSSS) program using persistent outreach between fall 2017 and winter 2018 were reviewed. This study answered the research questions: Which factors are significant predictors of students in the VSSS program? Do GPA, grants, and loans received differ for students in the VSSS program? Do GPA, grants, and loans received differ for first-generation status? and Do VSSS status and first-generation status interact in the effect on GPA, grants, and loans received? Comparisons were made between students who were (n = 103) and were not (n = 345) in the VSSS program. Binary logistic regression analysis revealed that race/ethnicity, first-generation, gender, grants, and GPA were predictors of VSSS participation. Our analysis found significant main effects for participation in VSSS and for first-generation status and the interaction of those two factors with GPA, loans, and grants. Because the VSSS provides support services, it indirectly addresses the stress of transition from "soldier to student" that leads to poor outcomes for veteran students.