This chapter examines the integration of artificial intelligence (AI) into medical devices and the regulatory complexities arising from the intersection of the European Union’s Medical Device Regulation (MDR) and the AI Act. It highlights AI’s transformative role in healthcare, from advanced diagnostics and personalised treatment plans to real-time patient monitoring. The discussion focuses on the challenges of dual compliance, emphasising the need for a balanced regulatory framework that fosters innovation while upholding rigorous safety and efficacy standards. Key areas of regulatory overlap—including risk classification, technical documentation, conformity assessment, and post-market surveillance—are explored in depth. Additionally, the chapter identifies implementation challenges such as ambiguous requirements, the intricacies of risk-based categorisation, the need for clearer conformity assessment guidelines, and the disproportionate burden on small and medium-sized enterprises. It concludes by advocating for the development of harmonised standards and comprehensive guidance to streamline implementation, ensuring a regulatory landscape that both promotes innovation and safeguards patient safety.