After a brief recap of the Italian legal framework in matter of employment subordination, the A. analyzes the three Judgments of the Italian Courts concerning the classification of on-demand work. The A. underlines the complexity of the classification of the new forms of work through the traditional criteria of interpretations, but he also criticizes the initiative of the Italian Legislator, which, passing article 2 Decreto Legislativo No. 81/2015, traced a doubtful boundary between the direction of work (still the essence of employment subordination) and the organization of other\u2019s work (a feature which should lead to the application of employment standards without losing the nature of independent contractor). Ultimately, the A. contends that the burden of finding an adequate response to the social needs of on-demand workers cannot be placed (entirely) upon the Courts, since it is a matter of policy (action) at large. Accordingly, he weights and eventually endorses the regulatory trajectory of conferring upon \u2013 certainly vulnerable, regardless of their classification as employees or independent contractors \u2013 on-demand workers a bundle of selected protections, through a \u201cad hoc\u201d statute and/or via collective bargaining