Aim: Taking a transactional approach, the present study sought to examine the extent to which perceived work environments, and appraisals of demand, play a role personality-stressor-strain relationships. Methods: The data were obtained from a sample of trainee teachers, enrolled in a demanding one-year postgraduate programme (N= 139). Survey methods were used to obtain dispositional measures (Neuroticism, Personal Control Beliefs and Interpersonal Control Beliefs), perceived work environment variables (stressor frequency, positive event frequency) and characteristic appraisals of demanding teaching situations. Low job satisfaction and psychological distress (GHQ-12) were measured as indicators of strain. Results: Two different models were specified and tested, using hierarchical linear regression analysis. The first, a "differential exposure-reactivity" model (Bolger and Zuckerman, 1995) was used to assess relationships between personality, perceived work environment, and the two strain outcomes. The theory underlying this model is that personality affects strain outcomes through increased exposure to demanding environments (mediation), and/or through increased reactivity to those environments (moderation). A further "differential appraisal- reactivity" model was used to investigate relationships between personality, appraisals of demand, and strain outcomes. Again, this model was used to test for both mediation and moderation effects. Different patterns of results were observed for each of the strain outcomes. However, in each case, the analyses indicated evidence of significant direct and mediated effects, with limited evidence of moderation. Conclusions: The present study suggests two possible mechanisms through which personality could affect stress-related outcomes. Research currently in progress is investigating dynamic, real-time person-environment transactions using Experience Sampling Methods. This research has implications for the role(s) of personality in the stress process, and also highlights the need to examine outcome-specific effects.