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The purpose of this phenomenological study was to discover the lived experiences of borrowers who struggle with student loan debt and repayment, giving voice to experiences not typically captured in quantitative studies. The theory guiding this study was phenomenology, which centered the meanings borrowers construct from their lived experiences of debt and repayment. The design of the study utilized a qualitative phenomenological research design. The central research question addressed was: What meanings do student loan borrowers assign to their experiences of struggling with student loan debt repayment, particularly in relation to their social, personal, and economic circumstances? Data were drawn from secondary public sources, including narratives obtained from podcasts, YouTube interviews, and journalistic features, yielding 18 participant narratives across 13 sources. Data were analyzed using Moustakas’s (1994) phenomenological method of horizontalization, significant statement extraction, and thematic clustering. The analysis revealed six overarching themes: the broken promise of education, the emotional and psychological weight of debt, structural entrapment within the repayment system, delayed and disrupted life milestones, financial illiteracy and the vulnerability of youth at signing, and racial and socioeconomic inequality amplified by debt. Findings indicated that borrowers assign meaning to their repayment experiences through a lens of betrayal, entrapment, and lost possibility, with implications for loan servicing practices, financial literacy education, and policy reform.