Since the introduction of digital media, design education has been challenged by the ongoing advancement of technology. Technological change has created unprecedented possibilities for designers to engage in the broadening realm of interactive digital media. The increasing sophistication of interactivity has brought a complexity which needs to be managed; most notably, information technology. The mobile device revolution has changed people's lives and created distinct challenges for design educators to master. Social media provide new possibilities as/for teaching technologies to engage students. On the downside, designers compete with amateurs through crowd-sourcing platforms. Responses to manage the rapid technological advance in design education have emerged as pockets of innovation from some institutions. This paper takes a closer look at how technology has affected and continues to affect design education in the context of design educators and practitioners arguing that design education is stuck in the past. Does every technological "revolution" require a radical change in design education? To answer this question the broadening and squeezing of design education is examined in the context of the increasing complexity of technology. Potential and "must have" responses to technological challenges are illustrated through examples from an undergraduate digital media design major.