This thesis examines the emerging legal and regulatory framework of the European Union on smart contracts through the lens of the technology-law interface. It explains key EU instruments such as the Data Act, MiCA, and GDPR, and unpacks their implications for blockchain-based contracting. The thesis sheds light on the sore spots of legal certainty, enforceability, and interoperability. It also identifies opportunities for harmonisation and proposes reforms for offering a more adequate fit for automated digital contracts within the EU legal order.