The purpose of this qualitative case study was to understand community college student success from the student perspective. Research questions included: (1) How do community college students define success? (2) What are student expectations facilitating success? (3) How do student perceptions of success, expectations facilitating success, and overall college experience influence student success, as perceived by students? Expansive research has provided insights into the contextual complexity of community college students served, varying missions of community college, and the pivotal role of engagement in serving underprepared and underserved students. This study utilized semi-structured interviews to gather in-depth data, guided by the psychology contract theory, to better understand how students perceived success, student expectations of the institution facilitating success, and how fulfillment of these expectations influenced student experience and overall success. Data provided insights regarding the varying goals of students and noteworthy impact of relational contexts of institutional agreements and fulfillment of expectations that are influential to success. Students articulated expectations, however, institutional agents’ understanding of students and expectations proved to be more influential on success than fulfillment. Student success remains complex and varies based on individual student goals. Students enroll with expectations of agreement with the institution, explicit and implicit, which influences success. The understanding of student needs and expectations and relational aspects of agreement proved most influential in student success.