The paper, after giving an overview of recent labour trends in the digital economy, describes alternative working arrangements such as “crowdworking” and “work on-demand via platform”. The regulatory framework and the legal consequences of such innovative and non-standard forms of work are analysed in detail with emphasis on the improper classification of workers in the gig-economy. In the second section, the essay focuses on the recent Communication of the European Commission on Collaborative Economy that is aimed at establishing under which conditions an online platform should be considered a provider of the “underlying services”. This focus is followed by an analysis of antitrust as well as labour law implications of Spanish, Italian and British rulings.The contribution explores the proposals on how to craft an intermediate category between employees and independent contractors. Workers in the on-demand economy have brought lawsuits alleging that the online platforms are misclassifying them as independent contractors, but the question remains still unsolved. Proponents recently advocated that a third category would be a good fit for digital platform work. Conversely, as far as Italy is concerned, the quasi-subordinate category created an opportunity for uncertainty and arbitrage resulting in the erosion of protection. The article describes the notion of the so called “collaborazioni organizzate dal committente” (contractors whose performance is organised by the principal) as a tool to expand crowdworkers’ rights.Finally, the most recent Italian labour market reform could eventually provide a solution for the current disputes on how work in the gig-economy could be regulated. In fact, the scheme of “collaborazioni organizzate dal committente” could represent a useful template, since it broadens the scope of the protections granted to standard employees.