The purpose of this collective case study was to discover the decision-making processes used by senior student affairs officers when making wicked decisions related to the retention of specialized, at-risk student populations. Wicked decisions are complex, resistant to resolutions, lead to other problems, and are essentially unique. In this study, decisions related to retention of Black males; students with mental health issues; and lesbian, gay, bisexual, transgender, and queer student retention fall within the wicked problem category and were the focus of this study. These decisions are usually the responsibility of divisions of student affairs in higher education settings and the senior student affairs officer. Hence, the senior student affairs officer is tasked with making responsible and effective decisions that foster the success of all students. This dissertation focused on the decision-making processes, practices, and procedures student affairs officers use to support the retention of select special populations served in higher education. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]