MiBoard (Multiplayer Interactive Board Game) is an online, turnbased board game that was developed to assess the integration of game characteristics Opoint rewards, game-like interaction, and peer feedback) and how that might affect student engagement and learning efficacy. This online board game was designed to fit within the Extended Practice module of iSTART (Interactive Strategy Training for Active Reading and Thinking). Unfortunately, preliminary research shows that MiBoard actually reduces engagement and does not benefit the quality of student self-explanations when compared to the original Extended Practice module. Consequently the MiBoard framework has been revamped to create Self-Explanation Showdown, a faster-paced, less analytically oriented game that adds competition to the creation of self-explanations. Students are evaluated on the quality of their self-explanations using the same assessment algorithms from iSTART Extended Practice module (this includes both word-based and LSA-based assessments). The technical issues involved in development of MiBoard and SelfExplanation Showdown are described. The lessons learned from the MiBoard experience are also discussed in this paper.