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This paper presents the way that an Index-Maximizing Linear Programming (LP) Model has been applied for dynamic reasoning in an intelligent Graphical User Interface. The graphical user interface is called I-Mailer and provides intelligent help to users during their interaction with an e-mailing system. For this purpose, I-Mailer constantly reasons about every user action in terms of the user's goals and plans. In case the user is involved in a problematic situation, it transforms the user's problematic action and generates alternative actions to be suggested to the user. The actions suggested should be better than the problematic one in the context of the user's hypothesized intentions. However, this process usually results in the production of too many alternative actions that could be suggested to the user instead of the one issued. To solve this problem, we have applied an Index-Maximizing LP model in order to select the best alternative actions to be suggested to a user.