The occupational environment may affect one’s psychophysical health by leveraging both external workplace stressors and individual psychological responses. We developed a comprehensive questionnaire to assess occupational stress among postgraduate medical trainees, investigating both situational and personal aspects. Exploratory factor analysis was used to identify the constructs captured by the questionnaire, and reliability was assessed by estimating Cronbach’s alpha. Construct-specific scores were computed, and their correlation with established pre-validated scales (criterion validation) was assessed. Four factors—“stress”, “coping”, “empathy”, and “trauma”—explained 50% of data variability and demonstrated satisfactory overall internal consistency (Cronbach’s alpha = 0.76). Significant correlations were found between the “stress” score and the “emotional exhaustion” component of the Maslach Burnout Inventory (MBI) (r = −0.76), the “coping” score and the “positive attitudes” component of the Coping Orientation to Problems Experienced Inventory (COPE) (r = 0.46), and the “empathy” score with the “empathic concern” (r = 0.52), “fantasy” (r = 0.41), and “perspective taking” (r = 0.45) components of the Interpersonal Reactivity Index (IRI). No significant differences in scores were found in terms of gender or medical specialization. This study suggests that the SCOPE questionnaire may be a promising tool for assessing workplace stress and psychological responses among medical residents.