Recent years have seen large-scale growth in the international school sector, with schools reporting increasing competition to recruit and retain expatriate teachers, particularly in hardship locations. Using a gap analysis framework (Clark & Estes, 2008), this study seeks to identify the knowledge, motivational, and organizational factors necessary for principals to be successful in their efforts to retain expatriate teachers in international schools in the sub-Saharan region of East Africa. Assumed causes were generated from a review of the research literature in this area and validated with data collected through interviews with principals, teacher surveys and principal surveys. This study suggests that, although principals possess understanding of the knowledge and motivation factors that contribute to teacher retention, they lack understanding of the relative importance of these factors. Furthermore, though principals are motivated to invest time and effort in the retention of teachers, this study suggests that organizational policy gaps exist in how the principals approach teacher retention in a strategic manner. The study concludes with a range of proposed solutions and a detailed implementation plan designed to assist schools in addressing the challenges that they face in seeking to leverage the work of principals in retaining expatriate teachers. [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.]