Since 2017, our organizations, Jobs for the Future (JFF) and Persistence Plus, have partnered to learn more about nudging and tackle two of higher education’s thorniest challenges: increasing racial equity and developing talent for in-demand jobs. Instead of trying to determine whether nudging works or not, we recently engaged in research to identify the conditions under which nudges work—or don’t work. That information could help schools design strategies for nudging students in a thoughtful, nuanced manner. Our findings indicate that nudges can become an invaluable tool for holistically supporting learners in career pathways programs.