Offering an overview of the interactions between digital technologies and contract law, we identify three pillars in this architecture: the regulatory framework; digital interventions over the life cycle of the contract; and digital objects of contracting. The regulatory framework, which itself may draw on digital technology to effectively pursue its ends, shapes, and is shaped by, the other two pillars. More specifically, on the one hand, we show how four key technologies – digital platforms, Big Data analytics, artificial intelligence, and blockchain – are being used at different stages of the contractual process (from the screening for contractual partners to formation, enforcement and interpretation) and engender novel market dynamics that, in many instances, necessitate regulatory responses. On the other hand, digitally facilitated contracting increasingly relates to digital content as the object of the contract; however, while this area has notably been the subject of the proposed Directive on Contracts for the Supply of Digital Content and thus has received some first ‘European structure’, we argue that a number of important blind spots remain that fail to be addressed by the directive. All in all, the use of digital technology in contracting will likely reinforce an adaptive, relational view and practice of contracting. This increased fluidity engenders a vast potential for preference-conforming, time-sensitive contracts; however, to the extent that it also mirrors novel asymmetries of information and power, the ordering mechanisms of the law may simultaneously be more needed than ever.