The transborder impact of information technologies on the economy across finance, entertainment, healthcare, and supply chains might be claimed to be meteoric. The effect of the digital environment advances companies through free competition. However, compliance with AI and blockchain technologies requires significant time, effort, and money. The use of AI and blockchain technologies also demands users for sustainability. This study introduces the legal challenges of financial technologies focusing on AI and blockchain systems for business and consumers. In this chapter, the features and usage era of AI and blockchain technologies are analyzed through economic and legal perspectives. Considering transboundary transactions of blockchain and AI technologies and relevant risks, revision on AI or blockchain-relevant law should take both domestic and international measures into account. Companies preferring to use financial AI systems that involve high risk are proposed to use blockchain technologies for technical surveillance countermeasures. In this regard, blockchain and AI might be an effective way to secure both consumer’s privacy, personal data, and companies’ any data relevant to transaction against threats such as computer intrusion. Accordingly, EU regulations are discussed to analyze AI liability. The chapter questions whether legislating and AI systems are justified with regard to conflict of the laws and difficulties on de-anonymization of blockchain-based transactions. This study analyzes the compliance risks of AI as a type of fintech and proposes regtech as a solution, introducing crypto courts.