The aim of this work is to investigate the factors promoting students’ engagement at school and supporting their well-being experience. According to the Positive Education there is a strong relationship between school environment and student’s well-being. Moreover, the quality of the school climate perceived by the students was found to influence engagement in school activities, as well. In this study, 153 students (M = 67) attending 10th grade were presented with tests and questionnaires to assess individual assets (personality traits, literacy skills), emerging appraisals (school-climate, well-being experience) and emerging actions (school engagement), according to the Student Well-Being Model. Path analysis showed that the best model does include neither individual assets nor direct effect of school climate on engagement, as the effect of school climate on engagement is mediated by well-being experience. The main result is that school climate has been confirmed as an important factor to be considered to improve engagement in school activities, but it is effective only when its influence can modify the well-being experience of the students. Moreover, the lack of significant effects of individual assets in the model suggests that improving school climate means to support well-being experience and, indirectly school engagement, irrespective to learning abilities and personality traits. This work encourages working in/with schools to implement positive education programs that support and sustain a positive school climate and culture for school-community wellbeing.