The purpose of the study is to investigate the relationship between the experience of conscripts in their training period and their subsequent attitude toward national military service immediately after training. Self-report questionnaire is used to measure the experiences of Estonian conscripts (n = 518) in three categories: perceived stress, applied coping strategies, and evaluation of training as important. Attitude toward national military service is measured as a critical versus neutral/positive answer to an open-ended question. We found that a perceived reduction in general quality of life, concerns about what is happening at home, and experiencing/expressing negative emotions were associated with a critical attitude. In contrast, taking a proactive outlook toward training and finding military-specific aspects personally important were associated with a more neutral/positive attitude. Our findings emphasize the importance of improving the conscription training experience in order to foster less critical attitudes toward service and are discussed from a person-environment perspective.