Through the introduction of the Digital Services Act (DSA), the European Union has established a comprehensive regulatory regime characterised by extensive due diligence obligations imposed on providers of intermediary services online. These obligations, now systematically codified in legislation, cover technical aspects of the provision of intermediary services, including duties to inform recipients, to adopt protective measures safeguarding users’ rights, as well as organisational requirements concerning the provider’s internal structure and system architecture. Furthermore, article 54 DSA introduces for the very first time a horizontal private enforcement system for all rights conferred upon recipients under this Regulation. Yet, this provision ultimately proves to be of limited practical utility. Unlike other provisions (such as article 82 of the General Data Protection Regulation), article 54 DSA refers merely to Union and national law without further elaborating or adapting the substantive content of the right to compensation under the DSA. Such a broad concept of the right to compensation, as set out in article 54 DSA, raises concerns regarding its coherence with other regulatory objectives pursued by the EU legislator. Moreover, leaving the determination of the conditions of liability in case of violation by the providers of their due diligence obligations solely in national law appears to be rather ineffective. Claimants are likely to face significant challenges, including for instance the burden of proving certain pecuniary damage and establishing the providers’ fault in breaching their duties. In this context, the present paper aims to examine the scope and substantive content of the technical due diligence obligations under the DSA and to assess how these obligations impact the foundation and practical enforcement of recipients’ right to compensation under article 54 DSA.