The essay analyses the prospects for circular integration between the regulations on health and safety at work and the anti-discrimination legislation to protect gender equality, in the national and international framework. Starting from a multilevel regulation approach, the analysis is conducted with particular reference to the case of harassment at work, as governed by ILO Convention No. 190/2019 and also referred to by the Italian rules on voluntary certification of gender equality contained in Law No. 162/2021 and in the UNI/PdR Guidelines 125:2022 and, more recently, supplemented by the Directive (EU) 2024/1385 and the international standard ISO 53800, containing guidelines for the promotion and implementation of gender equality and women’s empowerment. After an examination of the preliminary definitional issues of the phenomenon, in the broader scenario of psycho-social risks, the essay focuses on its regulation in the transdisciplinary context outlined above, paying particular attention to the different implications of the overall regulatory framework on prevention strategies vs. remedial perspectives and its protection apparatus. This aspect will be first analysed from an evolutionary point of view and then transposed into a critical and comparative analysis of the effectiveness of the different regulatory techniques—binding and voluntary—adopted in this area of labour law. Thereafter it will be shown that the assessment of the risk of harassment can play a crucial role in the process of adopting prevention protocols of organization and management models and management systems for health and safety at work. This risk assessment is also fundamental in the procedure that leads to certification of gender equality. In this context, precise assessment of the risk of harassment represents a conditio sine qua non for the issuance of the certification, together with training interventions on “zero tolerance” and the creation of a peculiar equality management system.