Background: Teachers’ health has emerged as a crucial topic of the quality of the school system. In fact, high rates of attrition and burnout among teachers have emerged to cause their turn-over, sick leave and early retirement, as well as poor quality of the educational activities. The role of negative emotions and feelings experienced at work, in fact, has undoubtedly proven to have a strong impact on the general health of teachers. On the other hand, studies on well-being have proven to offer important opportunities to set up effective policies dealing with public health. More specifically, the role of dispositional, positive affect, such as happiness and self-esteem, has proven to be linked to individuals’ health. Quite surprisingly, this link have not been addressed yet adequately among teachers. Moreover, observing the mediating role played by the teachers’ working environment between dispositional traits and their health may help to develop effective measure for improving teachers’ well-being and the educational attainments of their students. In this respect it is interesting also to operate cross-country comparisons, in order to shed a light on the possible different, effects due to the different educational system and cultural environment. Aims of the study: To develop an exploratory study, aimed at investigating the mediating role played by job satisfaction between teachers’ happiness and self-esteem on the one hand and their physical and mental health on the other. To compare India and Italy, in order to highlight the possible differences between the two countries. Methods: A questionnaire was administered, containing questions about participants’ background information and the following scales: the Job Satisfaction Survey, the Rosenberg Self- Esteem Scale, the Physical and Mental Health Scales (SF12), and the Ivens Scale in the Adapted Version for Teachers: School Children’s Happiness Inventory (SCHI). Participants were 300 primary and middle school teachers from the India and about 250 teachers from Italy. Results: Job satisfaction fully mediates between both happiness and self-esteem, and health teachers in both groups of teachers. Happiness and Self-esteem are linked positively to teachers’ health. Conclusion: Work is a relevant domain to promote teachers’ health, through job satisfaction.