The evaluation of educational work is one of the most pressing issues in education. Its implementation in Greece during the 2022-2023 school year, after a forty-year absence, presents a significant topic for both theoretical and empirical investigation. This study aims to explore this issue by first providing a theoretical examination of educational evaluation, clarifying key terms, and presenting its most critical aspects. The legal framework of teacher evaluation over the years is outlined, culminating in an analysis of the 2021 law, with its application examined through the research findings. The research part of this study investigates the perspectives of educators and administrators regarding the evaluation of educational work, particularly focusing on its implementation over the last two school years. The findings reveal that, in most cases, the evaluation was carried out in accordance with current legislation. However, certain aspects of the process, criteria, evaluators, and outcomes were identified as problematic or unclear, requiring improvements and clarifications to ensure the objectivity and effectiveness of the evaluation. Despite some concerns, teachers do not oppose the evaluation of their work; they consider it necessary and express a willingness to contribute their insights to the state, as they are the ultimate recipients and implementers of any educational evaluation legislation.