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Menu interface usability has been regarded as a critical factor affecting the quality of software applications. This paper developed a method for automatically generating intelligent and dynamic menu to reflect different needs from different types of end users. The contents and structures of the menu are dynamic and adaptive to the usage context (user and task). Such implementation was based on the Cognitive Walkthrough procedure and automatic instrumentation. This paper also described a pilot study performed to evaluate the effectiveness of the dynamic menu. Preliminary results showed that the dynamic menu interface reduced the time for menu search per task significantly than the normal menu interface. The total time for completing a series of tasks was also reduced significantly.