In Belgium, sex work was recently decriminalized to enhance street-based sex workers’ (SSWs’) health. This qualitative study explores stakeholders’ perceptions of the impact of the working environment on street-based sex workers’ occupational safety, health, and well-being in Brussels. In-depth interviews with seven stakeholders directly involved with SSWs were conducted, with data analyzed using qualitative content analysis. The analysis of study data resulted in one theme: “A power imbalance and a lack of concerted efforts among stakeholders are detrimental to the occupational safety, health, and well-being of street-based sex workers”. In Brussels, the majority of SSWs face various challenges due to structural vulnerabilities, thus limiting their choices regarding their work environment and further compromising their health. Limited access to resources and severe constraints within their working environment contribute to a lack of safety and adverse health outcomes. A stigma mechanism fueled by ideology and personal interests prevents the enforcement of their rights regarding their working environment, safety, and health promotion. The lack of involvement of key stakeholders, especially from the public sector, prevents the majority of street-based sex workers in Brussels from benefiting from a sound working environment and the promotion of their health, safety, and well-being.