The higher education industry uses the very latest technologies to effectively prepare students for their careers, but these technologies often contain vulnerabilities that can be exploited via their connection to the Internet. The complex task of securing information and computing systems is made more difficult at institutions of higher education due to philosophical traditions of academic freedom as well as growing budgetary constraints and intransigent stakeholder expectations of unimpeded access to educational and entertainment resources. This qualitative multi-case study examined small and private, non-profit institutions of higher education to understand the challenges that technology managers face in securing these systems. Technology leaders at eight of these institutions were interviewed to determine the priority of information security, operational barriers that impede the implementation of effective security controls, current problems and issues that inhibited security controls, and what additional resources were necessary to implement security controls according to best practices. Insights, innovations, strategies, and common issues were sought during the interviews to create a foundational conversation for stakeholders. The findings indicated that there were significant operational barriers to computing security at institutions of higher education. A lack of institutional support and comprehension was found at all of the interviewed institutions and education of leadership at all levels is necessary as a first step to the development of a strategy. Additionally, a formal security framework should be adopted that will serve as a guide and a means of feedback to these institutions. This work should enable Information Technology leaders in higher education to develop a vision that supports a holistic and organized approach to computing security. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]