A sample of 399 secondary school teachers (156 males, 243 females, 18 schools) responded to a survey questionnaire containing one measure of stress and two measures of strain. The Stressors in Teaching Scale (SITS), developed specifically to place work stress within the Scottish “teaching” context (Mulholland, 2005), gauged work stress. The General Health Questionnaire-30 (GHQ-30; Goldberg, 1972) and Glasgow Symptom Checklist (GSC; Mahmood, 1999) presented a unique opportunity to compare teachers’ perception of strain with a “general” and “clinical” population. Positive correlations were observed between work stress and strain. Perceptions of work stress and strain differed significantly according to teaching role. Quantitative job demands (e.g., “workload”) was the main predictor of strain, and middle managers, who held leadership and classroom teaching responsibilities, reported this feature of work and “changing demands” specifically, as significantly more stressful than senior managers. Middle managers’ experiences of work were reflective of a “pile-up” of stressors, indicative of quantitative and qualitative overload. Crucially, 22% of middle managers recorded strain scores (GHQ-30 case) indicative of psychiatric morbidity, and approximately 67% had experienced feelings of “personal ineffectiveness” and “depression” (GSC), normally associated with a “clinical” population. The unique interaction of “stressors” associated with teacher role, job demands, and job resources highlighted a range of risk factors (e.g., “workload,” “teaching-learning interface,” “professional ethos,” “change,” and “role”) that have the potential to affect health in the long term.