Automation in forming and performing contracts is proving to be a major revulsive for contract law. The use of AI systems in and for contracting means ‘distancing humans from contracts’ towards a hybridization between (human) autonomy and AI agency. That needs to revisit the meaning and significance of human-centric concepts, principles, and rules in contract law. This chapter traces how contract law needs to face and can solve the key dilemmas posed by automated contracting and the solutions provided for by UNCITRAL Model Law on Automated Contracting, the ELI Principles on Automated Decision-Making, and the ELI Model Rules on Digital Assistants for Consumer Contracts. One of the policy issues that best embodies the criticality of the challenge is the legal treatment of unexpected outcomes. Remedies range from those based on contract-law rules to those based on liability rules. Each risk-allocation solution has implications for legal certainty, predictability, the protection of interests, and the promotion of automated contracting in business practice.