In the United States, measuring and documenting institutional effectiveness in postsecondary educational institutions is not a one-size-fits-all process. Although this can be effectively accomplished in a variety of ways, the best approach for any higher education institution is one that is tailored to the institution’s unique environment and directly supports the its mission. Nevertheless, there are common factors that can greatly influence institutions’ ability to measure and demonstrate levels of effectiveness directly tied to student learning. This qualitative study was designed to gain an understanding of how factors within a higher education environment, including structure, practices and processes, can impact the institution’s ability to evidence institutional effectiveness related to student learning. The study examined institutional effectiveness as defined by the Southern Association of Colleges and Schools Commission on Colleges (SACSCOC), and reviewed specific components of student learning assessment through SACSCOC Comprehensive Standard 3.3.1.1 (Institutional Effectiveness – Educational Programs). The researcher applied a multi-site case study approach to gain an in-depth understanding of this phenomenon. Through purposeful sampling, seven higher education institutions were selected from the 2011/2012 SACSCOC Reaffirmation Class. The phenomenon was studied at each institution as a single case, and using Yin’s cross-experiment logic, a cross case analysis was also conducted. In addition, to attain the most compelling results from this multi-site case study, both literal and theoretical replication (Yin, 1989) was employed. The researcher concluded that there were four significant variables that impacted the ability of the institutions to sufficiently evidence institutional effectiveness associated with student learning. These variables included leadership, institutional culture, resource allocation, and the planning and assessment processes at the institutions.