The article offers a comparative assessment of the social protection granted to self-employed workers in the EU and Italian legal systems. It is structured as follows: first, the EU regulation in force is analysed to assess whether and to what extent self-employed workers can be considered entitled to social protection; second, self-employment under Italian law is analysed. The regulatory choices that set the Italian system apart from the current EU regulatory trends are highlighted, especially with regard to using self-employment as grounds for ad hoc regulation and not only as the other side of the coin in relation to standard employment. In fact, as of 2017, the Italian legislator has been providing self-employment an ad hoc regulatory framework, which, although not comparable to that for standard employees as to the level of protection ensured, nonetheless represents incipient protection specifically designed for self-employed workers. Subsequently, measures have been taken also to support self-employed workers during market transitions and joblessness, especially during the Covid-19 pandemic, which in turn made extraordinary measures to support self-employed workers necessary. Conversely, the EU legislator continues to focus on related albeit clearly distinct issues: the fight against bogus self-employment and the extension of social protection to particularly vulnerable workers who fall outside employment law’s scope of protection. The new directive on platform work is the most recent evidence of this: through an unprecedented system of legal presumptions, it seeks to bring platform work within the regulatory scope of standard employment. In light of the above, the paper’s conclusion frames self-employment as worthy of attention on the EU legislator’s part, especially in light of the European Pillar of Social Rights, not merely to avoid that standard employment’s stringent obligations are circumvented, but above all to issue ad hoc regulation that acknowledges and protects self-employed workers’ interests and acknowledges their social citizenship and dignity. Indeed, no conflict exists between extending the protection granted to permanent employees to new types of work and streamlining protection for self-employed workers.