Low-income, historically underrepresented, first-generation, and academically underprepared students are expected to attend college at increasingly higher rates in the coming decades, yet these high-risk students tend to graduate at lower rates than their counterparts, reflecting wider systemic inequities that persist in the United States. This study assessed the pathways to first-year success among 253 students from 5 institutions who identified as having 1 or more of these high-risk characteristics, examining the predictors of students' grades and intent to persist to the second year. The relationship of students' thriving levels to first-semester success was evaluated to add to previous studies that demonstrated the mediating role of Thriving Quotient (Schreiner, 2012) scores on student success outcomes. The following research questions guided this study: To what extent do thriving levels, entering characteristics, incoming perspectives on spirituality and mindset, and college experiences predict self-reported grades among high-risk students in the first semester of college, after controlling for their risk factors? and To what extent do thriving levels, entering characteristics, incoming perspectives on spirituality and mindset, and college experiences predict intent to persist among high-risk students in the first semester of college, after controlling for their risk factors? Hierarchical multiple regression analyses revealed the final models explained 29.3% of the variance in high-risk students' self-reported grades and 27.5% of the variance in students' intent to persist to the next academic year. Students' self-reported grades were predicted by high school grades (beta = 0.43, p < 0.001), Academic Determination scores from the Thriving Quotient (beta = 0.28, p < 0.001), working off campus (beta = -0.13, p < 0.05), and satisfaction with Student-Faculty Interaction (beta = 0.13, p < 0.05). Implications for practice centered on cultivating Academic Determination in high-risk students during the first semester and providing greater opportunities for rewarding student-faculty interaction. Students' intent to persist was predicted only by Institutional Integrity (beta = 0.39, p < 0.001), and household income (beta = 0.12, p < 0.05). Implications for practice centered on addressing high-risk students' perceptions of institutional integrity and meeting their expectations and needs for support. [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.]