This chapter explains a systematic way of conducting process evaluation of pen-based digital media-making projects using system dynamics modeling. The study aimed to understand student and teacher experiences and changes in behavior while engaged in the digital media-making process. Data was collected at a pen-based digital media-making summer program held at Pepperdine University´s Los Angeles and Ventura County campuses. After transcribing and coding raw data using grounded theory, the authors generated causal loop maps. The study indicated that the production of videos depends on both the students´ and teachers´ engagement in the digital media-making process. Active engagement of teachers and students improved the quality of the learning environment. The use of system dynamics allowed us to see the flaws and unique aspects within the digital making process.