When thinking about the past year for education services organizations, the movie Groundhog Day comes to mind. In the movie, Phil Connors, played by Bill Murray, is destined to repeat Groundhog Day, until he “gets it right.” He is stuck in an endless time loop because he keeps repeating past mistakes and can’t get out of his own way to realize a new and brighter present. Eventually, as all feel-good movies go, he finally “gets it right” and moves on to a new day, brimming with the hope of a fulfilling life. Like Phil Connors, education organizations seem to be stuck in the same endless loop. What is that loop? Applying what’s worked in the past to the present and thinking that what worked then will work now. And what is the present? The present is the conversion of many businesses from a capital expense (CapEx) business model, in which payment for products and/or services is upfront, to an operating expense (OpEx) business model, in which payment is subscription-based. This latter scenario is commonly known as XaaS—anything as a service. As time and data show, education organizations have been slow to adapt their processes and practices to support XaaS business models. Case in point, TSIA’s report, “The Education Services Adoption Playbook,” written in 2021, outlines nine plays that education organizations can employ to support XaaS models and product adoption. While TSIA understands that Rome wasn’t built in a day, using 2021 as a timestamp, many of the questions asked and problems experienced by education services members today are the same as they were four years ago. While this report could be a reiteration of the nine plays in “The Education Services Adoption Playbook,” it will zero in on three particular areas in which education organizations are stuck in the endless Groundhog Day loop.