Within the domain of geotechnical engineering, risk assessment is pivotal, acting as the linchpin for the safety, durability, and resilience of infrastructure projects. While traditional methodologies are robust, they frequently require extensive manual efforts and can prove laborious. With the onset of the digital era, machine learning (ML) introduces a paradigm shift in geotechnical risk assessment. This chapter delves into the confluence of ML and geotechnical engineering, spotlighting its enhanced predictive capabilities regarding soil behaviors, landslides, and structural resilience. Harnessing modern datasets and rich case studies, we offer an exhaustive examination that highlights the transformative role of ML in reshaping geotechnical risk assessment practices. Throughout our exploration of evolution, challenges, and future horizons, this chapter emphasizes the significance of ML in advancing and transforming geotechnical practices.