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Online readiness self-assessments are widely used in universities providing distant education, and they can help prospective students to understand the requirements and their readiness to study in these universities. Most of the self-assessment systems are Web-based static questionnaires. In this paper, a novel adaptive online self-assessment system AM I READY is introduced. The system is based on knowledge models, including static and dynamic user model, counseling model and self-assessment process model. It can dynamically filter questions to be asked to a specific user and adjust the contents of webpage dialog between the user and the system according to knowledge models and the user’s responses. The system is more effective and helpful than the usual ones.