PURPOSE: Residents in training have reported high levels of stress and anxiety and have a greater risk of mental health problems compared with the general population. Mental health problems among residents have been correlated with decreased professional effectiveness, increased medical errors, emotional exhaustion, and depersonalization and could have significant negative effects on future practitioners. The purpose of the present study was to identify the factors that might be associated with the mental health and satisfaction of oral and maxillofacial surgery (OMS) residents and to determine the associations between these factors and OMS resident satisfaction as a surrogate of resident well-being. MATERIALS AND METHODS: We designed and implemented an online survey, which was e-mailed to all OMS residents in the 101 accredited training programs in the United States. The survey was designed to determine and assess the factors associated with OMS resident satisfaction. Differences between groups were tested using 1-way analysis of variance for continuous variables and χ2 tests for categorical variables. For each factor, we fit a logistic regression model to estimate the odds ratio of resident satisfaction for the factor, adjusting for gender, year in residency, and years of advanced training. RESULTS: Of the 1181 resident surveys sent out, 300 were completed (25.4% response rate). The satisfied OMS residents tended to be men, further along in their training program, and to have access to mental health resources. Dissatisfaction was associated with greater self-reported stress levels, working a greater number of hours per week, and believing one would be viewed differently for speaking to faculty about mental health. CONCLUSIONS: OMS resident satisfaction was associated with identifiable and potentially modifiable factors. These factors included workload characteristics, stress and coping ability, and mental health impact and resource availability. Evidence-based strategies for OMS resident well-being could lead to the development of best practice guidelines for promoting and optimizing resident mental health.