With the wide spread adaptation of digital technology in the design discipline, there is a need to understand the role of technology in design teaching. In this chapter, we will examine the role of technology as probes, prototype, and toolkits and ask how this facilitates a more holistic learning process. "Design problem" is by its nature multi-facetted and open ended. The difficulty faced by most educators in the design discipline is that of encouraging students to develop critical thinking and approach the open-ended nature of their subject. We will explore making as a critical investigation of the design problem with two projects taught in an architectural design studio environment, at both undergraduate and graduate levels as case studies. By reviewing experiential learning through making, we can develop a more integrated means of teaching technology within a broader trans-disciplinary design context.