This dissertation focuses on digital platforms and apps connecting pools of workers, employers and clients instantaneously. These working arrangements call into question the suitability and effectiveness of the current employment legislation. The emerging literature reveals pervasive commands, reinforced surveillance, constant monitoring, arbitrary disciplinary action and very little or no workers’ discretion in deciding how to complete a task. Standard methods of social science research and legal analysis are applied in the investigation, accompanied by a strong interdisciplinary approach. With a law-in-context methodology, this study revolves around four main sections, each of them looking at platform-mediated work from a particular angle. After describing the theoretical antecedents of hierarchical outsourcing and relational contracts, Section 1 contributes to the literature on the “nature” of the “non-standard firm” by applying the economic analysis of transaction costs. Building on models on the disarticulation of the employing entity and the pulverisation of work-related responsibilities, this chapter conceptualises the prototypical business model of these new economic and social actors. The expression “Cerberus firm” is used to define a network company built as an online middleman that reduces information asymmetries, minimises organisational costs and engages a pool of providers (virtually recruited, effectively directed and persistently disciplined) through rapid transactions on the market with an authoritative attitude. Section 2 carries out a critical scrutiny of two myths: technological displacement and the crisis of the standard employment relationship. This assessment also requires looking into the contractual arrangements. The typologies of employment generated by the on-demand economy are part of a broader class of non-standard forms of work emerging from digitalisation. These organisational patterns manifestly exclude workers from employment protections and social security benefits. Accordingly, a picture of the spread of precarious employment is drawn, by taking into account as many alternative working formats as possible including self-employment work, economically dependent self-employment and disguised employment relationship. This review concludes by representing the employment relationship as a resilient and flexible tool, capable of adapting to the incessantly changing nature of production systems. Section 3 maps a kaleidoscopic array of app-distributed arrangements, clustering the findings into three main subsets (passenger transport services, professional crowdsourcing, on-demand work at the client’s premises). In doing so, the relationship between a worker and the platform is assessed along five main critical stages of the process, starting with the registration and ending with the payment. Several initiatives aimed at promoting fair and decent work in the collaborative economy are scrutinised, namely (i) the European Commission’s Communication 356/2016, (ii) the principles enshrined in the European Pillar of Social Rights, and (iii) the ruling by the European Court of Justice on the nature of the service provided by Uber. Furthermore, existing regulatory schemes, ranging from the Directives on atypical employment to other casual work templates, are assessed to test their resilience against this background. Section 4 investigates the legal status of platform-coordinated workers by considering what is at stake in pending litigations. In the end, this dissertation intends to “normalise” the discourses surrounding the digital transformation of work, by also contrasting the sense that new realities of work have outgrown legal concepts. This thesis argues that, before exploring captivating hypotheses for reforms, lawyers and scholars must seek to square this fast-evolving phenomenon with the existing legal framework. There is indeed the need for a balance between safeguarding social rights and unleashing authentic societal improvements. Several available legal notions and tools, which can adequately address this challenge, are discussed with a view of advancing a tentative regulative framework of platform-mediated labour.