It is common for enrollment management professionals to encounter challenges in process and practice when implementing new technical systems (Rowan-Kenyon, Martinez Aleman, and Savitz-Romer 2018). Challenges involving the implementation of a digital onboarding platform within established practices have potential consequences for both staff and applicants. These challenges also have significant impacts on the health of the institutional enrollment process as a whole. Using a university case study to illustrate the real-life manifestation of these challenges, this article lays out some of the most frequently encountered struggles surrounding new technology implementations and highlights key opportunities for addressing these issues.