Although the creation of a federal financial aid system in the United States has greatly expanded opportunity for students seeking postsecondary education, the higher education financing system faces a handful of problems in its current state. At the same time that the higher education financing system is facing these issues, an alternative to traditional student loans known as income-share agreements (ISAs) is gaining attention. There is currently a lack of federal legislation that provides a national framework for ISA providers and students to work within. Policymakers are considering this situation and attempting to address it in a way that properly balances the interests of both ISA student and lenders, but past policy in this arena has had a tendency to cause effects that were not intended. This study seeks to understand if there is a way that policy can be examined that allows for the identification of certain types of policy that result in unintended consequences before the effects go into place. In order to do this, I examine ten higher education financing policy cases over the past sixty years in an effort to establish a theory of policy that causes unintended consequences. I then test this theory using three interviews with higher education experts relevant to the ISA space in an attempt to see if this theory can be applied to additional cases, such as proposed ISA policy. I find that, although it is difficult to establish a theory that predicts if a policy will cause unanticipated results with certain, the findings from my case studies and interviews can serve as a set of lessons of what has worked well and failed in higher education financing policy. As applied to proposed ISA policy, I conclude that policy entrepreneurs in this space will face difficulty in adopting lessons from past policies due to the challenges to policy learning they face in the current legislative climate.