In 1971 Conceptual art curator-publisher Seth Siegelaub and lawyer Robert Projansky created The Artist’s Reserved Rights Transfer and Sale Agreement, a legal tool enabling artists to retain property and economic rights in their sold works. To Siegelaub, the “Artist’s Contract” would function as a clear statement of an artist’s desired rights, and its efficacy was ensured by the legal technology of contract and its promise of seamless and just transactions – “A perfect waffle every time!” However, the Artist’s Contract has been little-used and remains controversial, particularly for its stipulation for an artist’s resale royalty, and its demand for transparency in resales. Today however, numerous blockchain-based platforms for selling art employ smart contracts with terms similar to the Artist’s Contract. Here, resale royalties are not taboo, but are encouraged and enforced through the “promise” of smart contracts to automate a “perfect” transaction every time. But rather than rush to celebrate these technological potentials, might we pause to reconsider the value of contracts as systems of relations, rather than processes of automation, as law and society scholars have urged? These developments encourage a comparative view to historical contract technologies as we assess the unfolding implications of smart contracts and blockchain within the art market.