Higher education in Singapore has been closely aligned with the social and economic imperatives of the country throughout its history. From the establishment of the National University of Singapore in 1980 to the setting up of the Singapore University of Social Sciences as the sixth Autonomous University, the national drive to develop human resources with education as a vehicle has been key to the country’s success, but the increasing demand for university places, the impact of Industry 4.0, the dominance of ICT and the use of learning analytics have distinctly affected the way higher education has been delivered and to whom since the turn of the century. This changing landscape also calls into question both the nature and meaning of a university education. The focus on just-in-time learning and the provision of ‘stackable’ skills would likely leave learning gaps that a more traditional degree would find difficult to fill. This chapter begins with a brief review of the history of higher education in Singapore and considers its evolution amidst past and recent pressures. It further examines how local institutions have responded to the shifts and challenges that have accompanied the transformations in our environment.