Since 2012, City Health Works in Harlem, New York, has hired clinically supervised, neighborhood-based health coaches to support low-income patients manage chronic illnesses like diabetes and hypertension. Medication management is a major focus of this work. Here, we present the major reasons for medication issues, including those that required “escalations” to clinical supervisors. We also discuss the unique ways that community-based coaching can help address medication management challenges that emerge in patients’ daily lives (e.g., multiple medications or food insecurity). Finally, we recommend several action items for medical training and practice, aimed at improving the delivery of patient-centered care.