This chapter analyzes the legal and regulatory framework introduced by Article 9 of Italy’s “Decreto Dignità” (Law No. 96/2018), which imposes a broad ban on all forms of gambling and betting advertising, including indirect and digital promotion. The chapter examines AGCOM’s (Italian Communication Authority) interpretative guidelines and enforcement actions, especially regarding digital platforms. Notably, it highlights landmark rulings against Google and other tech companies, where courts reclassified them as “active hosting providers” due to their role in content promotion. These decisions mark a shift in EU jurisprudence on platform liability. The chapter also explores enforcement challenges, sanctions imposed, and the growing role of AI and automated systems in ensuring compliance.