Previous research showed that psychological detachment from work during leisure time is beneficial and that reflecting on negative aspects of work is detrimental for employees’ well-being. However, little is known about the role of positive reflection about work during leisure time. In the present research, we examined the effects of positive work reflection on affective well-being. Additionally, we tested the effectiveness of an intervention to increase positive work reflection and to improve well-being with a randomized controlled field experiment. Findings from three diary studies showed that positive work reflection was related to an increase in affective well-being with regard to both positive and negative mood. The results further indicated that the benefits of positive work reflection were incremental to that of psychological detachment and the absence of negative work reflection. Contrary to our expectation, no evidence was found for the effectiveness of the intervention. Theoretical implications of main findings as well as supplementary findings are further discussed.