This study assessed the effectiveness of a writing task designed to foster self-regulatory coping with stressful experiences to reduce medical clinic visits and to promote adjustment. Students entering college (N = 122) who were classified as optimists or pessimists by using a dispositional optimism measure participated in a self-regulation task (expressing thoughts and feelings about entering college and then formulating coping plans), a disclosure task (expressing thoughts and feelings only), or a control task (writing about trivial topics) for 3 weekly writing sessions. Among optimists, both the self-regulation task and the disclosure task reduced illness-related clinic visits during the following month; among pessimists, only the self-regulation task reduced clinic visits. In general, the self-regulation task beneficially affected mood state and college adjustment whereas the disclosure task increased grade point averages.