This study examined associations between sensation seeking and perceived need for structure, and changes in reported well-being among deployed soldiers. Participants (n = 167) were assessed before and after a six-month deployment to south Afghanistan. Results indicated that although well-being declined in the soldier sample as a whole following deployment, the degree of decrease was significantly different among soldiers with different personality profiles. Differences were moderated by soldiers’ level of sensation seeking and perceived need for structure. Results are discussed in terms of a person-environment fit theory in the context of preparation and rehabilitation of deployed military personnel.