Over the past 30+ years, many colleges have made themselves more accessible for adult students. These innovations include flexible scheduling, online learning, professionally-oriented degrees, and credit for what students already know. However, there is more work to be done, particularly in the areas of financial aid for the very large number of adult part-time college students, as well as in the areas of academic support and advising. But undoubtedly, these progressive changes have made it possible for many adults to get into school, stay there, and finish their degrees. In this article, the authors share two cases of individual students they worked with where they served as mentors in assessing prior learning. The two cases exemplify practical and academic innovations. In one example, a faculty mentor and student collaboratively improvise new learning within an individualized learning contract. The other example is about a mentor-evaluator and student discovering a new way to construe prior experiential learning neither had anticipated.