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In most parts of the world, minors’ access to education is guaranteed, resulting in most of their time being spent in the school building. Similarly, school staff spend a relatively long time in the same building. This unique setting requires both groups to stay inside the school walls throughout the working days, which might negatively affect their well-being. Studies show that low indoor air quality might negatively affect well-being. Moreover, school staff and students mention other problems, such as worrisome declining students’ attendance, motivation, social relations, safety, stress, and pressure, among others. Technological solutions, such as IoT-based systems, might be one way to tackle the well-being issue at schools. However, most of the existing solutions focus on the quality of the indoor environment, disregarding the needs and pains of school inhabitants. In the current article, we present an investigation of how IoT-based solutions could extend beyond solely environment-measuring tools and fulfill the needs of school inhabitants. Through an interview study with eleven IoT experts guided by user (school inhabitants) requirements identified in the previous research, we assess functional and non-functional system requirements that such systems should build on. These are discussed against the five-layer IoT architecture model. Moreover, the study identifies barriers and benefits of IoT-based solutions, which are discussed in the context of existing scientific and legal frameworks. The exploratory findings presented in the paper could be used as a guide for decision-makers at schools to ensure that the students’ and staff’s well-being is maintained, as well as by IoT suppliers to produce holistic or compatible solutions that could be easily integrated into the unique contexts of school.