Since architecture students studying design drawing are usually assessed qualitatively on the basis of their final products, the challenges and stages of their learning have remained masked. To clarify the challenges in design drawing, we have been using the BEAR Assessment System and Rasch family models to measure levels of understanding for individuals and groups, in order to correct pedagogical assumptions and tune teaching materials. This chapter discusses the analysis of 81 drawings created by architectural students to solve a space layout problem, collected and analyzed with digital pen-and-paper technology. The approach allows us to map developmental performance criteria and perceive achievement overlaps in learning domains assumed separate, and then re-conceptualize a three-part framework to represent learning in architectural drawing. Results and measurement evidence from the assessment and Rasch modeling are discussed.