Over the past decade, it has become evident that the financial sector’s landscape has undergone significant changes due to the advent of Artificial Intelligence (AI) and Machine Learning (ML). These twin technologies are responsible for creating a disruptive technological advancement in both the trading and wealth management verticals via algorithmic trading and Robo-Advisors, respectively. The usage of these technologies is providing several benefits and at the same time opening the doors for regulatory challenges. The benefits and challenges of these technologies are discussed through the lens of financial and technological adoption theories such as Efficient Market Theory, Behavioural Finance Theory, Innovation Diffusion Theory, and Principal-Agent Theory. This chapter of the book is influenced by Jane Street, a big international trading platform that earns billions of profits in the Indian Market in a fraction of seconds, which raises the concerns of Security Exchange Board of India, that such high-frequency Algo-based trading will effect retail investors. This study highlights the benefits and challenges and also provides the pathways to regulators to cope with this dilemma.