The world of student loans and debt forgiveness for teachers is a patchwork of overlapping programs, contradictory regulations, and expensive subsidies that date back to Dwight D. Eisenhower's signing of the National Defense Education Act of 1958. The 60-year experiment in using federal loan dollars to encourage students to become teachers could be poised for change as Congress considers reauthorizing the Higher Education Act. There is broad, bipartisan agreement that simplifying the nation's byzantine student-loan programs is an important goal. This article argues that lawmakers need to examine how these programs may have encouraged more teachers to pursue education master's degrees and driven up their price, and whether loan forgiveness programs actually fulfill their intended purpose--to recruit and retain teachers for the benefit of students. The reauthorization of the Higher Education Act presents an excellent opportunity for policymakers to create a clearer and fairer system with fewer hidden subsidies and perverse incentives. Doing that presents the need to ask basic questions, and preparation for large-scale change such as: (1) How should federal funds advance our education goals?; (2) Is paying for graduate school a sound investment in our nation's teachers and schools?; and (3) Do existing loan-forgiveness programs actually work, and how well? The article calls for advocates and policymakers to not let the prospective elimination of some programs be the enemy of simplifying and supporting others.