Many large urban school districts have implemented Early Warning Systems (EWS) in order to track and organize student data related to their progress toward graduation. The popularity of EWS has increased over the past decade as a number of research studies have demonstrated claims that the EWS data can be used to predict, to a certain degree of accuracy, which students will graduate on time (Bowers, 2010; Bruce, Bridgeland, Fox, & Balfanz, 2011). However, dropping out is not always a decision, but rather the outcome of a long journey of school experiences and life factors that set students on a path to become a dropout or graduate (Rumberger, 2011a). In this case study, interviews conducted with four twelfth-grade students reveal complex lived experiences related to their data in the EWS. This study used Dewey’s (1938) theory of experience as a theoretical framework to better understand how the students’ lived experiences help explain the data recorded in the EWS. Results of this study indicate that, while students describe similar objective conditions of school, they each walk into the school building with unique internal conditions. It is ultimately the interaction between each student’s internal conditions and the objective conditions in school that create the experience they have there. Without a better understanding of the interaction between a student’s internal conditions and the objective conditions that are influencing each student’s experience, districts and schools will be left with an intervention “guessing game.” It is the charge of educators in schools and at the district level to create processes that use the data in the EWS to develop improved practices in the school, and most important, the classroom. The data in the EWS are virtually useless if they do not lead to improved school routines and teacher effectiveness.