Residency is a pivotal phase in the journey to becoming an independent autonomously functioning family physician, marked by rigorous training, long hours, and immense pressure. Factors such as workload, hierarchy, and a demanding learning curve contribute to the complexity of residency, all of which can have a profound effect on the well-being of a resident and their future career aspirations. A struggling resident can have a significant impact on delivery of patient care and the collective well-being of the program. It is important for residency faculty to recognize and address the struggles of residents, foster a supportive training environment and ensure the delivery of high-quality healthcare. Identifying a root etiology or cause of a resident’s struggles can aid in crafting an individualized remediation plan. Clear processes for escalation of discipline are essential to this process for resident development as well as ensuring a safe, clinical learning environment.