High-quality student affairs programming and support services are indispensable to community college student success. Yet, while institutions establish well-structured assessment of academic programs, few engage in formal institutional measurement of student affairs and services effectiveness. This article shares two community colleges' stories of building assessment capacity and assessment implementation within student support services. Using a case-study approach, this work traces the assessment journeys of Eastfield and El Centro Colleges through the eyes of student affairs administrators. Challenges, successes, and lessons learned inform community college practices.