Social media platforms have long been considered as public squares, democratic spaces of public interest, where communities can gather and discuss matters relevant for every member of society. Yet new actors who are relevant for the space of online speech continue to emerge. A more recent category of such stakeholders is reflected by content creators. Also known as influencers, content creators are a new iteration of the gig economy engaging in the generation and monetization of user content. So far, research has very much focused on monetization from the perspective of content creators. In this working paper, I take the perspective of platforms in trying to better understand monetization policies. To this end, I focus on Twitter as an example of a platform with a blossoming content monetization strategy, which has also been seriously changing in the light of Elon Musks’s plans for the future of the platform. As monetization is becoming more and more complex, and it entails an increasing amount of transactions, it is important to understand what kind of frameworks platforms develop around their monetization products. The goal of this paper is two-fold: to understand content monetization on Twitter according to the platform’s own rules, policies and practices; and to highlight the complex legal framework that applies to content monetization from a transatlantic perspective. The paper is structured as follows. Section 2 offers a general overview on content monetization based on existing literature and taxonomies. Section 3 addresses Twitter monetization as a case study, and presents a methodology for the selection of platform documentation. Section 4 outlines some regulatory questions relating to monetization from the perspective of US and EU law, highlighting some essential concerns arising out of the increasing complexity of the relevant legal frameworks. Section 5 provides a brief discussion of the findings and concludes.