Although the nature of higher education and the students we serve have drastically changed since the passage of the 1965 Higher Education Act, little has changed regarding the award and disbursement of financial aid. In 1965, the typical college student was likely between 18 and 21 years old, living on campus, and a full-time student. In contrast, in 2016 almost 39 percent of all undergraduates were part-time students while in 2015 almost 29 percent of those undergraduates were 25 years old or older (Digest of Education Statistics, 2018). The traditional way of determining eligibility for and disbursement of financial aid is now significantly out-of-step with the undergraduates. The combination of older students, new types of credentials--especially short-term credentials taking less than a year to complete--innovative delivery methods such as competency-based education, the emergence of new providers, and the increasing need for students to gain new skills throughout their working lives is now out of step with the current federal financial aid system. Although some of these issues might be addressed through regulatory changes, Congressional action may be necessary. In order to prove access to the largest number of students, new regulations and types of financial aid should be considered in an effort to remove regulatory barriers to innovation including the continuation of year-round Pell, increasing aid to part-time students, and allowing students to access Title IV aid for post-baccalaureate programs. [Co-published with the University Professional and Continuing Education Association (UPCEA).]