This chapter first explores the lessons learned from the COVID-19 pandemic regarding digital transformation in higher education, and puts forward the next wave of digital transformation—emerging generative AI technologies (Sect. 13.2). The pandemic accelerated the adoption of digital tools, highlighting both opportunities and challenges in educational settings. While these technologies promise enhanced access, personalised learning, and improved engagement, they also present significant hurdles, including issues of academic integrity, inherent biases, and privacy concerns. As generative AI, particularly through large language models (LLMs) like ChatGPT, gains prominence, higher education institutions must adapt to its implications (Sect. 13.3). This chapter outlines key challenges associated with generative AI, such as the threat to academic integrity and the propagation of misinformation, while also identifying opportunities for enhancing inclusivity and personalised learning experiences (Sect. 13.4). Strategies for mitigating risks and integrating AI responsibly into educational frameworks are proposed, emphasising the need for ongoing dialogue, policy development, and curriculum innovation.