Increasing user engagement is constant challenge for Intelligent Tutoring Systems researchers. A current trend in the ITS field is to increase engagement of proven learning systems by integrating them within games, or adding in game-like components. Incorporating proven learning methods within a game-based environment is expected to add to the overall experience without detracting from the original goals, however, the current study demonstrates two important issues with regard to ITS design. First, effective designs from the physical world do not always translate into the digital world. Second, games do not necessarily improve engagement, and in some cases, they may have the opposite effect. The current study discusses the development and a brief assessment of MiBoard - a multiplayer collaborative online board game designed to closely emulate a previously developed physical board game, iSTART: The Board Game.