In the recent decade, the intermediary service providers have become increasingly intricate. While evolution of these intermediaries expanded access to creative works, they also posed challenges with unauthorised uploads of copyright content on their platforms. In 2022, the Digital Service Act (DSA) was adopted, aiming to establish new ISPs’ liability rules. Hence, the initial dilemma in copyright concerns the potential impact of the DSA on the liability regime for online content-sharing service providers set in Art. 17 of the Directive (EU) 2019/790 (CDSMD). One could argue that there is no intersection between the DSA and the CDSMD since the DSA is lex generalis regarding the lex specialis nature of Art. 17 of the CDSMD. However, according to the analysis in this chapter, the answer is not straightforward given, that there are various legal considerations for a different standpoint. Considering the DSA’s impact on the liability regime of the CDSMD, many dilemmas emerge. Addressing these dilemmas, this chapter will scrutinise relevant shortcomings of Art. 17 of the CDSMD, focusing on the liability regime and the general monitoring problem. After that, it will examine the DSA provisions that may intersect with Art. 17 of the CDSMD.