The paper addresses the problem of fraudulent contracting of work in the Swedish road freight transport industry with a focus on false (bogus) self-employment. The aim is to discuss the widersocial context of the problem and to illustrate the significance of the mandatory Swedish notion of employee when identifying and tackling misclassification of drivers’ employment status. By analyzing a case in this industry that has been tried in the Swedish Labor Court, and a related case that resulted in conciliation, the paper illustrates both the strength and limitation of labor law for couteracting disguised employment. The study also exemplifies why the notion of employee has been an argument against new regulations aimed to protect workers in the grey area between emploment and self-employment. In addition to written sources, the paper draws upon interviews with informants from the Swedish Transport Workers’ Union, the industry and the Swedish Tax Agency.