Higher education costs in the United States have increased by 69% in the last decade. Simultaneously, state legislatures have decreased the level of funding provided to institutions of higher education while states have initiated campaigns to encourage students to obtain a post-secondary education. With increased costs, decreased support, and enhanced pressure to attend college, students rely heavily upon student financial aid to cover college expenses. Currently, the aggregate federal student loan balance in the United States is $1.4 trillion. Because institutions depend upon student tuition dollars and most students must borrow money to afford college, institutions of higher education have a responsibility to ensure students have a strong understanding of their borrowing obligations. This study, determined the level of understanding of Montana undergraduate students, 18 years or older with student loan balances have of their student financial aid obligations and the factors that may influence their understanding. Statistical analyses found that Montana undergraduate students misrepresent their actual student loan balances by 23.5%. There was no relationship between the confidence students had in their perception of their loan balances and debt deviation. Moreover, 1 in 5 students who had a debt deviation of 31% or more expressed confidence in their ability to accurately report their student loan balances. This study determined that students who had loans outside the student federal aid program were more likely to have higher loan debt deviation and that upperclassmen were more likely to have lower loan debt deviations. This study also determined that students who had met with a financial aid counselor while in high school were more likely to have a lower debt deviation. Early interventions are necessary to help students improve their understanding of their financial aid obligations. Building high school and college partnerships would ensure that students have practical and personalized assistance in their first interaction with student financial aid. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]