Background and Objective: Ergonomics programs addressed to children and school-community fit the Health Promoting Schools (HPS) framework. Beyond the integration of ergonomics in curricula, important aspects regard the evaluation of the appropriateness and effectiveness of the programs. A correct evaluation of effectiveness is crucial to guide resource allocation, an essential step to implement and sustain the HPS approach. With the present pilot study, we aimed to evaluate the effectiveness of the program proposed to a sample of school children in the metropolitan area of Cagliari. Methods: The awareness educational program was designed along the lines of the National Institute of Work Accident Insurance (Italy) scheme and proposed to 260 middle-school children. The program is divided into three phases: i) assessment of students’ background, ii) displaying of the training modules, iii) evaluation of conceptual understanding. For this purpose, we used pre- and post-intervention questionnaires. Results: The results show a substantial improvement in the percentage of correct responses in the post-intervention, confirmed by the chi-square test, for questions regarding general concepts about ergonomics, backpack weight, and handling. On the other hand, some questions show a pre- and post-intervention continuity in terms of percentage of correct answers. We can divide them into two categories: a) questions to which the students already answered well (basic rules of polite postures); b) questions to which students often answered incorrectly, both before and after the intervention (illustrations; sequences). Conclusions: Effectiveness evaluation led us to a necessary re-evaluation of topics, form, and clearness of the questions posed, as well as of the teaching style. Adapting the program to the educational, environmental, and cultural context seems to be crucial for maximizing effectiveness. This pilot study demonstrates that the cultural gap relating to health and safety at school might be reduced with dedicated and tailored programs for school children and community.