This chapter aims to provide new qualitative evidence on the use of automated technologies in the cleaning industry, a sector characterized by gender and racial segregation and traversed by trends towards increased competitiveness and workforce flexibilization. With the emergence of multinational global players, a process of capital centralization coupled with the adoption of new models of work organization and labor management is underway. However, this sectoral reconfiguration has not resulted in concrete improvements in workers’ material conditions, but rather in workload intensification and the weakening of workers’ rights due to labor market deregulation and the spread of outsourcing practices. Looking at the adoption of new technologies, several interesting findings emerge, starting with the still limited diffusion of cleaning robots due to the unpredictability of physical environments, the crucial role played by manual dexterity, and the possibility for companies to rely on a flexible and low-paid workforce. Moreover, despite the high incidence of occupational hazards, health and safety issues are not significantly addressed when technological innovations are adopted. The data also highlights the weak role of unions, which are usually not involved in defining implementation strategies.