This dissertation consists of three papers that explore the open enrollment process in a large urban school district that has a mandatory choice open enrollment policy. The first paper examines patterns of school selection in this district after the introduction of a "strategy-proof" deferred acceptance student assignment algorithm. Because of the presence of this algorithm, families in this district can be expected to reveal their genuine preferences for the school program choices that are offered to them, presenting a unique opportunity to gain insight into how families choose schools. Overall, I find that the ways in which families select schools may limit the positive impact of open enrollment policies on racial integration in district schools. The second paper focuses on families' enrollment responses subsequent to student assignment. I examine the extent to which families attrite from the district or successfully obtain reassignment into another school after being assigned to one school; I also determine the conditions that are associated with greater likelihoods of families taking these actions. I find systematic patterns of enrollment responses that might negatively impact diversity within schools and the district as a whole. The third paper uses the results of the first two papers to construct an agent-based model of the open enrollment process in this district. I find that there is a large amount of stability in enrollment patterns over a simulated ten year period. When I simulate trends in enrollment patterns under policy conditions that the district might consider implementing, I find that engagement efforts that successfully get all families in the district to participate in the school choice process has the largest positive impact on diversity in the district and that replacing information given to families about school achievement levels with school value-added measures causes the largest reduction in the gap between the achievement levels of the schools in which White and Asian students enroll and the schools in which Black and Hispanic students enroll. [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.]