The transition from electronic commerce to automated contracting challenges the traditional notion of (human) autonomy and its pivotal role in Contract Law. Automated contracting means that human autonomy and AI agency interact in as yet uncertain ways, which could be ones of tension, conflict or, perhaps, symbiosis in the future. Contract law should be sensitive to these forms of hybridization, and adapt if necessary. Preserving and protecting human autonomy does also mean combating old and new forms of vulnerability. This Paper aims to trace the transition from electronic commerce to automated contracting and unveil the two-sided impacts on vulnerability risks. Looking closely at both UNCITRAL MLCA and the ELI DACC, the Paper focuses on three main dilemmas. First, legal recognition of automated contracting, party autonomy, and the right to use automated systems. Second, allocation of unexpected action risk, impact on autonomy and a new forms of vulnerability. Third, automated contracting and consumer protection paradigms. Contract law is facing today a profound and fascinating challenge to react to, accommodate, or embrace automated contracting and AI Agents in decision making.