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This paper describes the adaptation of a cognitive theory, called Human Plausible Reasoning (HPR), for the purposes of an intelligent graphical user interface (GUI). The GUI is called intelligent file manipulator (IFM) and manages files and folders in a similar way as the Windows 98/NT Explorer. However, IFM also incorporates intelligence, which aims at rendering the interaction more human-like than in a standard explorer in terms of assistance to users' errors. IFM constantly reasons about users' actions, goals, plans, and possible errors, and offers automatic assistance in case of a problematic situation. HPR is used in IFM to simulate the reasoning of users in its user modeling component and the reasoning of human expert helpers when they try to provide assistance to users. The adaptation of HPR in IFM has focused on the domain representation, statement transforms, and certainty parameters. The certainty parameters of HPR have been combined in a novel way with user stereotypes and the simple additive weighting theory. IFM has been evaluated and the evaluation results showed that IFM could generate plausible hypotheses about users' errors and helpful advice to a satisfactory extent; hence, HPR seemed to have fulfilled the purpose for which it was incorporated in IFM.