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Using a case study approach, this study explored the experiences and perspectives of 14 academic advisors and 3 advising directors as they implemented academic probation and dismissal policies. Guided by street-level bureaucracy theory, this study documented advisors’ humanizing approach to implementing academic probation and dismissal policies and how they used their discretion when making critical decisions for students’ academic trajectories. Three approaches to academic advising emerged: implementers, humanizing bureaucrats, and agents of change. The findings from this study have implications for reframing the terminology, purpose, and practice around academic probation and dismissal.