This paper describes our experience developing a custom LMS/IPAS system—the School of Social Work information System (SSWiS)—that was designed specifically for student learning, faculty advising, and academic administration within our social work graduate program. We present the challenges that motivated the design of SSWiS before describing the architecture and functionality of our solution. We then discuss our preliminary evaluation results. We conclude with a discussion of the benefits and limitations of our system in the context of today’s technical needs in graduate education in social work and other fields.