Completing a post-secondary degree is crucial to being competitive in the current job market. By 2020, the majority of all jobs in the United States require post-secondary education and training; however, barriers to access and attainment exist among individuals working to obtain post-secondary degrees, and there is an overall slowdown in post-secondary attainment. Students entering college identified as under-prepared is one of the attainment barriers to a post-secondary degree. This is particularly problematic at open admissions institutions like community colleges. When students arrive at college academically unprepared, they are often required to take developmental or remedial education coursework. In response to the low completion rates of developmental education, specifically in math, Illinois passed the Postsecondary Workforce Readiness Act. This act included Transitional Math courses taught during the senior year of high school. The intent of the PWR is to evaluate students' math proficiency during their junior year and enroll them in a Transitional Math course while still in high school. The 2019-2020 school year was the first year of Transitional Math implementation in Illinois. The purpose of this study was to investigate the eligibility and enrollment trends in Transitional Math in Illinois during the 2019-2020 school year. This quantitative study used data from one community college network in the collar counties of Chicago. [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.]