Despite the growing demand for Information System professionals, student enrollment in Master of Science in Information Systems (MSIS) programs has not risen proportionately. One fundamental reason is our inadequate understanding of the actual motivations and goals of the aspiring graduate students – a topic that we attempt to delve into in this research in progress. We utilize the Theory of Planned Behavior as the theoretical underpinning and create a survey instrument to assess factors that influence students’ motivations and propensity to pursue a Master in IS. Our research design further attempts to subdivide and compare the differentiated motivations of students with or without an academic background in IS. In this current report, we present the background of our research, our hypotheses, some initial insights from the on-going data collection process, and our research plans moving forward.