Since failure, over and over and over again, is a prerequisite to becoming an expert, so to is the ability to persevere and remain motivated through failure. Many researchers creating ITSs have taken the approach of manipulating the task in terms of difficulty, focus, and other parameters in an effort to sustain users' motivation. There are numerous circumstances where this approach is impractical, undesirable, or simply impossible. This task-manipulation approach misses the important opportunity to help users develop skills to deal with failure and frustration. We propose instead an approach that uses affective agents 1 to help users develop metacognitive skills such as affective self-awareness for dealing with failure and frustration. An important element of our approach is the use of one or more affective agents as peer learning companions to facilitate development of empathetic relationships with learners. This paper describes work in progress exploring how characteristics of affective agents can influence perseverance in the face of failure. Introduction: We choose to focus on motivation through failure because of its importance in the learning process. At Stanford's Department of Mechanical Engineering there is a saying that, "Spectacular failure is better than moderate success." (Faste, 1996) This is not an overtly masochistic agenda, rather the message is that if you do not strive for spectacular success you will never achieve it; if you achieve moderate success you have not strived far enough." Kay's version of this sentiment is that, "difficulty should be sought out, as a spur to delving more deeply into an interesting area. An education system that tries to make everything easy and pleasurable will prevent much important learning from happening." (Kay, 1991) In Csikszentmihalyi's words this would be the notion of matching adequate challenge with skill in service of Flow, or optimal experience (Csikszentmihalyi, 1990). In this vein, in their chapter on Motivation and Failure in Educational Systems Design Roger Shank and Adam Neaman describe the utility of simulated Learning By Doing environments, to accelerate the pace of learning through exposure to difficult circumstances that may arise less frequently than in real world situations. This will inevitably accelerate the rate of failure and, if motivation is sustained, the rate of learning as, "novices are exposed to rare, but critical, experiences" (Schank, Neaman, 2001). Shank and Neaman acknowledge that fear of failure is a significant barrier to learning and believe this can be addressed in several ways: minimizing discouragement by lessening humiliation; developing the understanding that consequences of failure will be minimal; and providing motivation that outweighs or distracts the unpleasant aspects of failure. They show that they have been able to sustain the motivation of learners, who care about what they are doing, by providing them access to experts at the time of failure. Through questions, stories, anecdotes and additional experiences learners are given the opportunity to, "expend the effort to explain their failures". Learners are given the opportunity to achieve and become expert (Schank, Neaman, 2001). Many have taken the approach of tailoring the task to the individual user in an effort to maintain motivation, an affective state, Flow or optimal challenge (Malone, 1981; Monk, 2000, Hill et al., 2001). Hill et al. in their paper, Toward the Holodeck, discuss the merits of the creation of a Holodeck like setting in terms of its immersive, believable, and motivating qualities. This terminology is remarkably similar to descriptions of psychological Flow. 1 Affective Agents can sense users' affect and respond with displays of their own affect .