As of March 2019, 43 million Americans held student loans provided through federal government programs, the largest segment of the education loan market. But this system is under pressure as more borrowers struggle to repay, a problem compounded by the complexity of the repayment process. Research on the pathways borrowers take through the repayment process, the decisions they make, and the barriers they encounter is limited, making it difficult for policymakers to develop evidence-based, cost-effective solutions to these and other challenges. To help fill this information gap and better understand where public policy can have the greatest impact, The Pew Charitable Trusts commissioned the Trellis Company, a Texas-based organization that acts as a guarantor for the Federal Family Education Loan (FFEL) program, to conduct an analysis of almost 400,000 borrowers in that state (referred to as "Texas borrowers" throughout the paper) during the five-year period beginning when their loans entered repayment anytime between October 2007 and September 2011. This analysis concentrates on Texas, rather than the nation as a whole, because Trellis has a rich administrative dataset and similarly robust data were not available at the national level. The key findings about the Texas borrowers are: (1) Approximately a quarter of borrowers defaulted within five years of entering repayment; (2) Those who owed more than their original balances after five years in repayment--21 percent of borrowers--had frequently missed and paused payments; and (3) Almost half of borrowers had paid down some principal after five years. This analysis aims to give researchers and policymakers a better understanding of how people interact with the student loan repayment system and why they might face serious challenges. The findings of this report point to three actions that the Department of Education and Congress could take to boost repayment success among borrowers who struggle with delinquency, default, and growing balances: (1) Identify at-risk borrowers; (2) Provide servicers with resources and comprehensive guidance; and (3) Eliminate barriers to enrollment in affordable repayment plans. This report examines some of the significant challenges that borrowers face as they navigate the complexities of the repayment system and the recommendations for actions that policymakers can take to promote successful repayment among the nation's millions of student loan borrowers.