The proliferation of contracts that are used in the contemporary world to facilitate the trade in goods and services is significant. Notably though, the world is rapidly transitioning from the traditional industrial-based economy to the new digital economy. This article will examine these vulnerabilities as they relate to the rise in the use of artificial intelligence (AI) for the development and administration of digital contracts. Digital contracts are those contracts developed and managed through and by technology. The article draws on examples from the United States (US) and the European Union (EU). The importance cannot be underestimated, because the transition from the traditional method of developing, negotiating and executing contracts today, is rapidly evolving. Generally, the human element of contractual negotiations has, in part, been diluted, and is being replaced by technology. It is the technology that the contract negotiator is using to develop the contract, rather than in person. Nonetheless, the use and application of technology in contract development paved the way for potential data and cybersecurity concerns. The article concludes by arguing that the common law and the Convention on the Sale of Goods 1981, in relation to damages for a breach of contract, are well equipped for the AI systems that are used to generate and execute commercial contracts. Thus, it can be viewed that a contractual liability for damages under common law exists, whether through human agents or through AI systems. This article concludes by suggesting further research needs to be undertaken to better understand the connection between law and technology. It also proposes that organizations embed risk standards into their operating procedures for developing and managing digital contracts.