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The paper examines the Court of Florence’s recent ruling in the judgment of opposition to a decree pursuant to article 28, law no. 300/1970. The most interesting aspects of the decision appear to be those regarding the identification of individual and, especially, collective protection granted to hetero-organized collaborators, including the feasibility of the appeal pursuant to article 28 of Workers’ Statute against conducts carried out by clients of hetero-organized collaborations; secondly, it deals with the issue of selecting the trade unions qualified to conclude a National Collective Labour Agreement pursuant to article 2, paragraph 2, legislative decree no. 81/2015, with particular regard to the distribution of the burden of proof on the greater representativeness in comparison; finally, the issue of the legitimacy of the Assodelivery-Ugl Rider National Collective Labour Agreement is dealt with, with particular regard to the stipulating union’s lack of representativeness and authenticity.