Although Hawai'i suffers from a chronic teacher shortage similar to the rest of the country, there are variables that make Hawai'i's dilemma unique. Between 2015-2020, there were over 1,000 teaching positions unfilled, with more than a third of positions being specific to special education (HIDOE Employment Reports, 2015-2020). In 2019, the Hawai'i DOE reported 94% of their teachers as highly qualified, however, that percentage dropped to 84% for the field of special education. One of the primary drivers of the teacher shortage is teacher attrition. In Hawai'i, attrition accounts for about 88% of the annual demand and is caused most by teachers who leave the profession prematurely and many choosing to leave the state. Attrition rates are doubled for teachers who were not trained by a local teacher education program. The College of Education at the University of Hawai'i at Manoa (UHM) is the largest local producer of newly certified teachers in the state each year. The targeted population for this study were 959 individuals who had started an application to a UHM special education teacher preparation program between 2015-2020. This mixed-methods exploratory sequential design study (qual [right arrow] QUAN) examined applicant characteristics, motivations for entry, and program preferences. A sub-analysis determined if significant differences in motivations or preferences existed among targeted subgroups currently underrepresented in the teacher workforce in Hawai'i (i.e., nontraditional, male, minority, geographically isolated). As a final analysis, all variables were examined to determine if characteristics, motivations, or preferences impacted enrollment outcomes. This study served to better understand who expressed interest in pursuing the special education profession and why, as well as, to better understand what they wanted in a program in order to pursue it. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]