This chapter enquires about the practical implications of making contracts smart. To many, any questions about the desirability of expressing contracts in code may seem like unnecessary academic nit-picking by someone who “clearly does not understand the unstoppable potential of the crypto economyCrypto economy.” Code is, after all, supposed to remedy commercial uncertainty and guarantee performance. Code is, if one follows the dominant crypto-narrative, the solution to most of the world’s problems! The simple question about the reason why contracts should be made smart may, however, lie at the very core of the misunderstandings surrounding smart contracts. Both lawyers and crypto-enthusiasts often overlook the important distinction between the source of contractual obligations and the expression of such obligations, not to mention the distinction between the tools used to perform an obligation and the contract itself. They also seem to assume that the manner of expressing a contract can guarantee its performance… In reality, the fact that an obligation or a contractual term are expressed in code can hardly be regarded as beneficial. Once a contract is expressed in code, the risk of breach is effectively replaced with the risk of programming errors, incorrect compilation or the unexpected execution of code.