This dissertation is comprised of three studies that examine the likelihood of exiting the college-going pipeline, test the framing of a text messaging intervention, and explore the transition and enrollment experience for high school seniors eligible for Tennessee's tuition-free college scholarship, TN Promise. In a discrete-time survival analysis, I use TN Promise scholarship eligibility as a proxy for remaining in the college-going pipeline and find that the odds of scholarship eligibility loss are lower for women than men, higher for Asian and Black students relative to White students, and higher for first generation college students. In a randomized control trial, I find that consistent, strategic framing of informational text messages during the college transition does not affect the likelihood of successful college transition and persistence. However, heterogeneity analyses reveal that, at certain eligibility checkpoints, certain treatment arms had small, negative effects on men, first generation, and Black participants. In a qualitative study, I find that Promise programs may reshape the expectations that students have for support from the state and their institution of enrollment. Taken together, these findings have implications for the timing and nature of eligibility requirements for Promise scholarships, the provision of support services by postsecondary institutions, and the framing of Promise programs by their sponsoring entities. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]