As the origin of directed self-placement (DSP), Grand Valley State University is in the unique position of having created, adapted, and maintained a DSP program for almost thirty years. This article explores the history of GVSU’s placement practices to articulate what we have learned about DSP amid our institution’s changing academic landscape. Using interviews and reflections from past and current administrators who lead our placement practices, we demonstrate that the philosophical foundation of DSP—student self-efficacy—remains the guiding light of our placement practices. However, we argue that multiple changes experienced at many institutions, including new admissions standards, changing student demographics, and the lingering effects of the COVID-19 pandemic, require WPAs to consider new questions about DSP to ensure that our placement practices promote equity and access to all students.