The article analyses, from a unions’ perspective, how overwork performed remotely contributes to hybridising employees’ status. More precisely, the paper studies how unions perceive remote overwork and examines the extent to which they find that this phenomenon blurs the boundaries between subordinated work and self-employment, lowers social protection, and challenges traditional forms of representation. The analysis is based on empirical data involving union officials and shop stewards of the quaternary sector in Milan. It was collected using a mixed-method approach that included a survey, eighteen interviews, and two participatory meetings. First, research participants stressed that overwork performed remotely undermines established social rights resulting from previous union achievements, such as the right to sick leave and breaks during the working day, while it also questions the remuneration of working time. Second, the article highlights the mechanisms identified by unions that contribute to working overtime when being remote, stressing that several of these factors correspond to characteristics of self-employment. Lastly, the paper analyses the extent to which remote overwork challenges unions, which not only see the deterioration of hard-won social rights but also find it difficult to create consensus and defend employees’ contrasting interests.