Given current global uncertainty created by sluggish economies and challenging job markets, the ability of students to repay their loans is not always clear, nor is it clear whether these loans contribute to their careers and lives. This study attempts to clarify these issues using data from the “Survey on Attributes of Student Loan Repayers” (2017) conducted by the Japan Student Services Organization. This study assesses the realities of loan repayment based on information collected at the time of the loan application and examines the impact of student loans on the lives of Japanese students. The analysis reaffirms that employment status and a stable income influence loan repayment. However, it also highlights the significance of the loan recipients’ awareness and involvement in the application decision and the application process, revealing that awareness and involvement at the time of the application impact future repayment. Moreover, the evaluations of the value of student loans reveal that while delinquent borrowers highly value the loans for enabling them to pursue their further education, they see less value in the loans regarding their ability to study more and thereby improve their learning outcomes.