Although much research has been devoted to positive emotions and how they foster Information Systems (IS) use and continuance, less is known about the role of negative emotions and their impact on IS discontinuance. Thus, based on theories in environmental psychology towards the role of emotional valence, a research model is developed to explain the effect of cognitively appraised emotional valence on IS discontinuance. To test our hypotheses, we have conducted a laboratory experiment with eye tracking and evaluated users’ emotional valence objectively based on their facial expressions using FaceReader, a facial expression analysis software. Preliminary results of our study suggest that users’ initial emotional responses evoked by unexpected opposing features of the IS, when first encountered, do have significant effects on subsequent avoidance behavior. The results also reveal that cognitive system appraisal seems to influence users’ emotions and behaviors differently depending on the type of the system for the task at hand. For example, we reveal that if IS are enhanced by hedonic design elements (e.g., pictures, graphics, video files), these elements could also trigger negatively valenced emotion if they are assessed as hindrance for the achievement of one’s objectives.