Ensuring smooth transitions to college may be difficult for the children of immigrants since their families are likely unfamiliar with the U.S. system of higher education, which is horizontally stratified and requires a number of steps before admission. Bridging social science literature on immigrant assimilation, cultural, social, and human capital, and college choice, I study the pathway to college among immigrant youth, focusing on heterogeneity by generation and legal status and how community and state contexts moderate educational outcomes. In the first paper, I explore inequalities in college knowledge using data from the High School Longitudinal Study of 2009. Specifically, I examine whether 11th graders can accurately estimate tuition and fees at two- and four-year institutions and the expected earnings of various levels of educational attainment. The second paper builds on the first by testing for heterogeneous treatment effects of social interactions in high school using the Education Longitudinal Study of 2002. If there are differences in college knowledge, it is possible that discussing college with teachers, counselors, or college representatives has disproportionate impacts for the children of immigrants. Since 2001, 27 states have passed policies that limit or facilitate college access for undocumented students. Some states have banned them from receiving in-state resident tuition, while others allow it and provide financial aid. The final paper uses survey data from the Current Population Survey and administrative data from California and Texas to determine whether these policy regimes affect college choice and preparation for likely-undocumented Mexican and Hispanic youth. The findings from this dissertation may prove useful to practitioners and policymakers interested in improving the knowledge acquisition, academic preparation, and enrollment decisions of the children of immigrants, a group comprising nearly a quarter of schoolchildren today. [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.]