1.0 Abstract Research has indicated the beneficial nature of optimism when presented with stressful situations by acting as a protector against adversity, resulting in the implementation of more effective coping strategies. The objective of this study therefore was to ascertain whether an additional measurement of an individual’s dispositional optimism accounted for any added variance when assessing the already well documented relationship between an individual’s personality and coping strategies on their academic performance, perceived stress and psychological wellbeing during their transition to university. One hundred and twenty four first year undergraduate students from the University of Edinburgh completed a longitudinal study during their first semester at university. Measures of personality, coping strategies, perceived stress, psychological wellbeing and available social support were assessed during the first two weeks of the semester. Perceived stress, psychological wellbeing, coping strategies and perceived social support were measured again at the end of the first semester, with academic performance being assessed using the results of the Psychology 1 exam. Results indicated that an individual’s dispositional optimism only accounted for additional variance in relation to their psychological wellbeing, demonstrating that a pessimistic attitude resulted in a greater level of stress during the major life transition of starting university. Personality was indicated to be the strongest predictor of perceived stress and psychological wellbeing and also the only significant predictor of academic performance. Interestingly, emotionally stable individuals performed worse than neurotic individuals on their Psychology 1 exam.