The demand-control/support model of work stress was tested in a sample of 419 correctional officers. The results suggest a link between certain work characteristics (high demands, low control, and low support) and strain symptoms (e.g., psychological distress, job dissatisfaction) as well as with negative affectivity (NA). On the other hand, other job characteristics (high demands and high control) were associated with positive behavioral outcomes (seeking feedback, looking at work as a challenge). Workers in high-isolation strain jobs with the greatest work exposure showed higher levels of strain and NA than workers with less experience working in the same job. Results suggest that work experience may affect long-term personality evolution. It is concluded that studies that control for the nuisance aspects of trait NA may underestimate the impact of the work environment on strain.