The ability of artificial intelligence (“AI”) to autonomously, or in response to specific prompts by human users, generate text, music and images, is developing at a breathtaking pace. Generative AI applications such as ChatGPT, DALL·E and Stable Diffusion are presenting new scenarios that can be confounding to copyright lawyers as well as judges and policymakers. This two-part article discusses whether existing copyright doctrines can adequately address these issues and to what extent a recent overhaul of the Copyright Act in Singapore in 2021 is equipped to deal with these challenges. Part 1 deals with copyright infringement in both the input of works to train generative AI applications and the AI output in response to human prompts and commands. Part 2 discusses how the computational data analysis exception and open-ended fair use provision in the Copyright Act 2021 are likely to apply to these scenarios.