Prompt template for a fictitious LLM agent in a content-flagging experiment

Abstract: Digital regulations such as the European Union's Digital Services Act (DSA) represent major efforts to shape human-centered and human rights-based frameworks for society. Yet, as these laws are translated into practice, challenges emerge at the intersection of technology, law, and design. This paper presents a qualitative case study examining how designers act as mediators between abstract legal requirements and real-world digital experiences for users, focusing on the design of content reporting mechanisms under Article 16 of the DSA. Through an expert workshop with professional designers from diverse fields (N=9), we explore how legal obligations are interpreted by designers and reflected in discussions and design solutions. Our findings resonate with previous research on the design of reporting mechanisms and dark patterns, highlighting how UX design choices can mislead or hinder users' decision-making and therefore also highlighting the crucial role of design decisions. We show how participatory design methods can bridge disciplinary divides, making legal obligations accessible in compliance fostering design solutions. By using legal design as a lens, we argue that the co-creation of digital regulations and user experience is a core site for digital humanism; where designers, engineers, and legal scholars must collaborate to ensure that systems uphold legal standards to address the challenge the regulation poses to these disciplines.