This paper investigates the effects of personality characteristics on individuals’ abilities to resolve ambiguity in an information retrieval environment. In particular, this research examines the effects on query performance of the interaction of personality characteristics (as measured using the NEO PI-R) with information requests that contained extraneous, syntactic, or both extraneous and syntactic ambiguities. The results indicate that ambiguity affected performance. The results also show that various personality dimensions significantly affect end-users’ abilities to compose accurate queries. Neuroticism, agreeableness, openness to experience, and conscientiousness affected the number of errors made in the query formulations. Conscientiousness affected the length of time taken to compose the queries and neuroticism affected the confidence end users had in the accuracy of their queries. In addition, the results indicated that, while the personality dimensions affected performance, there was no interaction between the personality dimensions and ambiguity.