This work begins with an introduction that describes the Digital Services Act (DSA) & Digital Markets Act (DMA), the aims as well as regulation targets of these two European Union (EU) legislations, defines what is understood under online content sharing platforms (OCSPs), and elaborates on the freedom of the media in times of rapid digital transformation. Its research objective is best explained by referring to the two central research questions. The first one addresses the DSA’s new key obligations for communication platforms compared to previous EU regulation. A second research goal questions how the DMA’s gatekeeper and level playing field provisions affect large communication platforms in comparison to preceding EU law. Representing the heart of this work, the analysis starts examining core provisions relevant for communication platforms, important previous EU legislative measures, and ends by discussing them critically. It kicks off with the DSA followed by the DMA. In terms of previous EU law, the e-Commerce (Electronic Commerce) Directive, the Audiovisual Media Services Directive (AVMSD), and the Regulation on Preventing the Dissemination of Terrorist Content Online (TERREG or TCO) are particularly important for the DSA as a comparison. Concerning the DMA, specifically its relationship to EU competition law, is examined. Subsequently, the conclusion answers both research questions as well as shortly delineates what is next by mentioning upcoming EU regulatory challenges and efforts in the form of the ‘European Media Freedom Act (EMFA)’ proposal. Finally, an outlook focuses on the latter legislative initiative and provides a tentative preview of digital services’ evolution in the EU.