Smart contracts are computer protocols that self-enforce encoded terms. They arguably allow for individual freedom and increased sovereignty from inconveniences. The enthusiasm goes as far as foreseeing that smart contracts will make contractual legal oversight obsolete. However, whereas contract law theory evolved to acknowledge the importance of flexibility and relationality, smart contracts activists defend the opposite direction, arguing for contractual rigidness and denial of social norms supporting complex transactions. This paper departs from this paradox to argue that (i) smart contracts based on existing technology are unlikely to thrive in complex contractual settings, and (ii) contextual analysis is important for LawTech’s propositions.