The transition from adolescence to adulthood can be difficult for many students, particularly those with mild disabilities. It's an unfortunate reality that students with disabilities continue to perform lower in terms of post-school outcomes in comparison to their peers without disabilities. The issue of improving post-school outcomes for students with disabilities has been explored since the 1980's and remains a central focus in public education that is reflected in local level decisions, policy initiatives and legislative changes as recent as July 1, 2021. While students', parents', and special education teachers' perspectives and their decision-making towards transition planning have been discussed within the literature, principals' perspectives and their decision-making on transition planning remain undetermined. The purpose of this study was to determine secondary principals' perspectives and their decision-making towards transition planning for students with mild disabilities. A survey research design was used to conduct this study. Data were collected using the "Principal's Perspectives and Decision-Making Survey" distributed to 113 secondary principals in Northwest Florida. Three hypotheses were tested using a combination of descriptive and inferential statistics that included a analysis of variance (ANOVA), and Mann Whitney U using The Statistical Package for Social Sciences (SPSS) 28. Results from the ANOVA revealed no significant mean differences existed in secondary principals' perspectives based on gender certification or years of professional experience. However, results from the MANN Whitney U and quantitative research from the survey responses revealed mean differences in principals' decision-making towards transition planning for students with mild disabilities. [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.]