When is reappraisal—reframing a situation’s meaning to alter its emotional impact—associated with psychological health? To answer this question, we should consider that reappraisal is a multicomponent process that includes, first, deciding to attempt to use reappraisal and, second, implementing reappraisal with varying degrees of success. Although theories of emotion regulation suggest that both attempting reappraisal more frequently and implementing reappraisal more successfully are necessary to achieve greater psychological health, no research has directly tested this assumption. We propose that daily diaries are particularly well suited to assess these 2 components because diaries can capture repeated attempts and success in daily life and with relative precision. In a sample of community adults (N = 219), we found that among participants experiencing elevated life stress (but not among those experiencing lower life stress), attempting reappraisal more frequently was associated with fewer depressive symptoms for those who used reappraisal more successfully, but was associated with somewhat more depressive symptoms for those who used reappraisal less successfully. These findings suggest that attempting reappraisal is associated with benefits only when individuals can implement it successfully. Thus, to fully understand the health implications of emotion regulation, we must consider it as a multicomponent process.