ClassDojo is a classroom communication and behavior management app intended to "bring every family into [the] classroom" (www.classdojo.com). The features of the platform include a points system to facilitate classroom management, instant teacher-parent communication (on the individual or class level), and student portfolios (among others). While ClassDojo claims to be used in over 95% of schools in the United States, there is little known about how students or principals interact with and understand the platform's features and data. Drawing upon a mixed-methods study in a small state in the Southeastern United States, this article offers empirically driven insight into how students and principals perceive new digital education apps like ClassDojo. In particular, this analysis speaks to stakeholder attitudes toward the use of the app with regard to if and how it is mediating student-teacher and student-parent relationships. In so doing, this article offers early insights from a state-specific case into how the use of and experience of ClassDojo is situated within the broader educational experiences of students.