This dissertation is based on an empirical study that focused on student reenrollment, an essential but largely overlooked element of school choice policies. Based on the school choice literature, I extended the hypothesis of parental charter school choice to the subject of reenrollment. In doing so, I referred jointly to theories from the fields of public choice and business, in order to better understand student reenrollment in a maturing education market. By tracking student enrollment records over multiples years and linking them to school attributes (socio-economic status, racial/ethnic composition of the student body, school quality label), student demographics, and student academic performance, I established a complex student reenrollment database. I applied a rigorous statistical model to this data, allowing me to identify a number of important insights about student reenrollment in a maturing education market. I described the reenrollment patterns at the state level, as well as a predictive model of reenrollment outcome at the individual level. My analyses indicate that student reenrollment was the most common school choice outcome: most students reenrolled in their present schools, regardless of that school's quality label; however, the student reenrollment rates in charter schools were lower than those in traditional public schools. I observed patterns of segregation in student reenrollment within Arizona, as reenrollment appeared to be significantly polarized with respect to school attributes and students' characteristics. There were two distinct patterns that appeared to coexist in Arizona's student reenrollment data: quality-oriented reenrollment and similarity-oriented reenrollment. The findings of this study extend the school choice literature to include student reenrollment. This study challenges the application of market metaphors in the context of school choice, which generally advocate the reform of public schools through encouraging students to switch, promoting school competition and thereby improving public education quality. Instead of using command and control policies to shame schools into improvement, however, policymakers and parents should employ school accountability policies and the practice of school labeling as a trigger to reinvest in struggling schools, rather than encouraging students to find a new one.