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In order to move the dial on postsecondary student retention, a quantitative study was conducted with hierarchical logistic regression analyses to predict both first-time freshmen students’ likelihood of being placed on academic probation and their subsequent risk of institutional departure. Tinto’s (1975, 1987/1993) interactionalist theory of student departure was used to identify predictor variables at time of entry into university and after entry. Predictors included demographic characteristics, academic indicators, college of entry, and academic major change. Though the strongest predictors were academic factors, the study also highlighted inequities in student success outcomes. This study has implications that will support institutions in cultivating a more equitable educational experience for students on academic probation by improving retention rates and reducing opportunity gaps.