In the past three decades, researchers have noted the limitations of a problem-solving approach that overemphasizes algorithms and quantitation and neglects student misconceptions and an otherwise qualitative, conceptual understanding of chemical phenomena. Since then, studies and lessons designed to improve student understanding of chemistry has overwhelmingly targeted introductory level, high school and first-year college students. In this article, we present a model-based learning cycle approach with upper-level undergraduate and beginning graduate students that investigated their ability to model the adiabatic and isothermal compression/expansion of a gas in a syringe. We were interested to observe, given the extent of their previous chemistry coursework, how students struggled to connect macroscopic observations with particulate representations. Analysis of laboratory reports, reflective journal entries, and classroom discourse transcripts indicate the learning experience was efficacious in uncovering and addressing student conceptual challenges with using models appropriately to describe gas behaviour under the experimental conditions for this investigation.