Technological advancement has significantly transformed commercial transactions through the emergence of smart contracts, blockchain-based systems, and Artificial Intelligence (AI). Smart contracts operate through self-executing code deployed on blockchain platforms and automatically perform contractual obligations upon the fulfilment of pre-determined conditions. AI, on the other hand, enhances commercial activity through predictive analysis, automated decision-making, fraud detection, contract management, risk assessment, and data-driven business processes. These technologies have improved speed, transparency, accuracy, and efficiency in commercial dealings. However, their growing use also creates important legal challenges concerning enforceability, consent, liability, jurisdiction, consumer protection, cybersecurity, data privacy, and algorithmic accountability. This paper critically examines the legal implications of smart contracts and AI in commercial law with special reference to India and selected comparative jurisdictions, including the United States, the European Union, the United Kingdom, and Singapore. It analyses the applicability of the Indian Contract Act, 1872, the Information Technology Act, 2000, and the Bharatiya Sakshya Adhiniyam, 2023 to electronic contracts, digital records, and automated commercial transactions. It also considers recent international and domestic developments, including Regulation (EU) 2024/1689, commonly known as the EU Artificial Intelligence Act, India’s AI Governance Guidelines, and the RBI’s FREE-AI framework. The paper finds that existing Indian laws provide partial recognition to electronic contracts and digital records but do not comprehensively address decentralised execution, coding errors, autonomous decision-making, algorithmic opacity, or cross-border dispute resolution. It recommends a technology-neutral statutory framework, sector-specific AI governance standards, stronger cybersecurity and data-protection safeguards, and specialised online dispute-resolution mechanisms to ensure legal certainty, accountability, consumer protection, and responsible technological innovation in commercial law.