Healthcare training environments, particularly in multidisciplinary training settings, present unique ethical dilemmas as a result of the multiple relationships faculty must balance while working with trainees. The historical and current perspectives on multiple roles in training environments will first be summarized. Evidence of a gap between the extant discipline specific guidelines and the realities of situations that occur in healthcare training will then be revealed, as illustrated in a case example. Primary care medicine training environments are highly nuanced, potentially leading to an infinite number of ambiguous situations that require a generalizable model for managing multiple roles. Rather than recommend specific modifications to existing ethical guidelines, a new model emphasizing role awareness and decision making when challenges in healthcare training settings arise is proposed. Recommendations for the case example using the model are offered. All professionals are prone to boundary transgressions; explicit training about and the maintenance of appropriate role balance will help to ensure high-functioning relationships and maximize the quality of patient care, resident education, faculty and resident satisfaction, and modeling of professional behavior to improve competencies as clinicians and educators.