Although research has explored what college students struggle to understand about financial aid, no research has investigated how at-risk students on financial aid probation articulate their financial aid knowledge and the gaps in that knowledge. As a result, this content analysis investigates online discussion board posts from a credit-bearing student success course for at-risk students (GPA < 2.00 or below a 67% completed over attempted credit hours ratio) to learn how these students conceptualized their financial aid knowledge and how prior knowledge could have helped them before reaching probationary financial aid status. This study involved 110 students across three semesters in the midst of the COVID-19 pandemic. Findings suggest students lacked financial aid knowledge to plan their college career, specifically with student loans. They relied on a range of familial resources, but were often unaware that their academic progress was tied to their financial aid. Implications for research, policy, and practice are addressed.