The illumination of a scene influences how that scene is scanned and how it is depicted. This premise, together with assumptions regarding implications for teaching observational drawing, was the basis for a pilot study in the Nova Scotia College of Art and Design (NSCAD) Drawing Laboratory. The pilot provided evidence that helped refine the question and methods described in this expanded study. As in the pilot, participants worked from common stimuli that were lit in two distinct ways. The participants drew for a predetermined period of time while their hand movements were recorded digitally and the entire process was observed firsthand. Over a period of 7 days, five participants each completed four drawings. The 20 drawings were compared and the recordings analyzed. Digital analysis generated the most informative data in that, while light’s influence on drawing strategies proved to be less significant than anticipated, changes in drawing behavior were observed with implications for teaching and learning.