Teacher burnout is a critical issue worldwide, leading to teacher shortages and high turnover rates. Although theoretical perspectives often highlight the influence of contextual factors on burnout, the role of (positive) organizational characteristics is frequently overlooked, with most focus placed on individual factors. The HEalthy and Resilient Organization (HERO) Model suggests that healthy organizational resources and practices contribute to developing healthy employees and achieving organizational success. Our study aimed to adapt and evaluate the Portuguese version of the HERO Check diagnosis tool. We also explored the relationship between organizational demands, resources, and practices and teachers' (un)well-being and performance in a subsample of education professionals. Our sample consisted of 1,295 Portuguese workers (74.7% female, M = 49.17 years, SD = 10.22), comprising 924 teachers and 371 general workers. The HERO check tool consists of three questionnaires: Healthy Organizational Practices and Resources (job demands, job resources, and practices); Healthy Employees (personal resources and (un)well-being); and Healthy Organizational Outcomes. Factor analysis confirmed the structural validity and reliability of the questionnaires. Structural equation modeling revealed an acceptable fit of the theoretical HERO model for applied settings. Multi-group invariance was attained across gender, work context, and instructional level. Comparative analyses indicated that teachers perceived higher job demands than non-educational workers, but perceived similar levels of job and personal resources, (un)well-being, and organizational outcomes. This suggests that while support structures were perceived as similarly accessible, the specific pressures of education appear to be more salient. Additionally, healthy organizational practices were perceived as underdeveloped across Portuguese workplaces. Regression analyses supported the predictive role of organizational demands, resources, and practices on teachers' personal resources, (un)well-being, and performance. These findings underscore the importance of context-sensitive tools in assessing and promoting healthy workplaces. Addressing teaching demands while strengthening organizational resources is key to retaining and engaging teachers effectively.