Academic underpreparedness is an issue for many first-time-in-college students, particularly those entering community colleges. Whereas many underprepared students enroll in developmental education, research has indicated that traditional remediation may not increase students' chances for success. Therefore, states and colleges have begun to implement new course placement strategies to increase the accuracy of initial course placement and new instructional approaches to better serve their developmental students. Specifically, in 2013, the state of Florida passed Senate Bill 1720 which redesigned developmental coursework and placement policies across the Florida College System. The reform lifted developmental education placement exam testing and course enrollment requirements for certain exempt students, irrespective of prior academic preparation or achievement. The current study focuses on these exempt students--those who had the option to bypass developmental education--who were also underprepared, and their initial course selection and subsequent success in their gateway (introductory college-level) English course. Using statewide student-level data and logistic regression techniques, the results indicated that level of preparation was related to students' course enrollment and gateway English course success. Students slightly underprepared in reading or writing were more likely than severely underprepared students to enroll in the gateway English class, relative to a developmental reading or writing course. In reading and writing, slightly underprepared students were more likely to pass English, relative to severely underprepared students. The authors consider the findings in light of recent national changes to developmental education and offer recommendations for policy and practice.