Student attrition poses a major challenge to academic institutions, funding bodies and students. With the rise of Big Data and predictive analytics, a growing body of work in higher education research has demonstrated the feasibility of predicting student dropout from readily available macro-level (e.g., socio-demographics or early performance metrics) and micro-level data (e.g., logins to learning management systems). Yet, the existing work has largely overlooked a critical meso-level element of student success known to drive retention: students’ experience at university and their social embeddedness within their cohort. In partnership with a mobile application that facilitates communication between students and universities, we collected both (1) institutional macro-level data and (2) behavioral micro and meso-level engagement data (e.g., the quantity and quality of interactions with university services and events as well as with other students) to predict dropout after the first semester. Analyzing the records of 50,095 students from four US universities and community colleges, we demonstrate that the combined macro and meso-level data can predict dropout with high levels of predictive performance (average AUC across linear and non-linear models = 78%; max AUC = 88%). Behavioral engagement variables representing students’ experience at university (e.g., network centrality, app engagement, event ratings) were found to add incremental predictive power beyond institutional variables (e.g., GPA or ethnicity). Finally, we highlight the generalizability of our results by showing that models trained on one university can predict retention at another university with reasonably high levels of predictive performance.