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Digital games are ideal for training complex decision making skills because they allow players to experience decision making processes and consequences. However, training complex skills often results in failure, which may undermine learning engagement. Traditional training methods employing observational learning (eg, training videos) do not cause learners to fail but forfeit experiential learning that makes training games so engaging. Our exploratory work addresses the trade-off between experiencing and observing failure and explores their effect on the level of training engagement. Building on past engagement research, we argue that learning engagement contains both cognitive and affective facets and that these facets may diverge, especially when individuals experience failure. To test these ideas, we conducted an experiment (N= 156) comparing engagement in game-based training, in which participants experienced failure, and video-based training, in which participants observed failure. We collected cognitive and affective indicators of engagement using physiological and self-report measures. We found game-based experiential learning increased such indicators of engagement as attention and temporal disassociation even though players widely failed to meet game objectives. Players also experienced elevated arousal and decreased positive affect. In addition, we compared physiological measures of engagement with self-reported measures and discuss their merits and limitations.