In this paper, we study the relation between the user's degree of understanding and his/her eye movements; in an effort to realize a proactive interface that monitors the user and provides a contextual support. The application is a gaze sensitive dictionary that helps the user when reading a text in a browser's window. Not only is the user's gaze analyzed but also the context and thus the difficulty degree of the text being read. The experiment results suggest using regressions as an indicator to trigger the help process along with a context grounding approach.
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