Due to the complexity of the contemporary world, the design process has shifted from its former reliance on fixed principles toward the outlook of Design Thinking, a shift that has brought about extensive transformations in design education Design Thinking is a form of pre-reflective awareness that serves as an internal compass along the path of design, which is referred to as design meta-awareness. This approach is capable of cultivating within the individual a key tool such as proportion, whose task is to objectify the designer’s mental images. Nevertheless, instruction based on Design Thinking is not simple, and the design teacher must take multiple factors into account. Teaching proportioning on the basis of Design Thinking is an internal process rather than an external prescription. Accordingly, the aim of this study is the internalization of proportion in freshman undergraduate students on the basis of the teachings of Design Thinking. At the outset, this study examines the literature of Design Thinking through a descriptive-analytical method in order to extract strategies for cultivating the mechanism of proportioning. In the next step, these strategies were tested experimentally on freshman architecture students at Payame Noor University. The findings derived from the research literature indicate that, in the internalization of proportion, the following strategies should be taken into account: release after learning, architectural education within the building atmosphere, the apprenticeship approach, and intra-group interactions. Testing the aforementioned strategies among Payame Noor freshmen provides architecture teachers with a diverse toolbox of guidelines for the internalization of proportion.