Student loan debt continues to grow at a rapid pace (Scott-Clayton, 2018). The total debt burden for each student graduating from college is over $35,000, and that number is likely to gradually rise as tuition costs and fees at institutions of higher education increase (Friedman, 2018). The problem is not that students accrue debt but rather the inadequate methods and assumptions students use to determine whether they can afford the loans they accept (Abraham et al., 2020).Many students have too little information related to student loan programs and display inflated expectations of earnings after graduation (Loonin & Morgan, 2018). The purpose of this study was to employ grounded theory within a qualitative framework to better understand how students calculate affordability in their specific circumstances. The key research questions asked how students determine the student loan debt they can afford, what their income expectations upon graduation are, and what effects discussion of student debt cancellation has on their perceptions. Through the use of an iterative interview process with 10 participants attending either public or private 4-year institutions, the researcher gained insight into the specific factors that students consider when determining student loan affordability. The researcher examined the thought processes of individual students related to the key research questions, and the results point to new pathways for strengthening educational programs that instill sustainable borrowing habits in students who require loans to finance their education. [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.]