Education of health-related professions such as medicine, nursing, dentistry, pharmacy, etc. represents a major category of adult training. Cognitive flexibility theory which emphasizes a case study based approach involving context-dependent and realistic situations applies directly to health care education. COFALE is an adaptive e-learning environment supporting cognitive flexibility. In this chapter, we present EX-COFALE, an extension to COFALE. COFALE, although offers facilities for adaptive content presentation, adaptive use of pedagogical devices and adaptive communication, it lacks facilities for adaptive student assessment. EX-COFALE remedies this deficiency of COFALE by allowing for automated test creation and assessment based on the students’ knowledge information. To this end, COFALE has been modified to allow for representation of associations between test questions and learning concepts. Also, assessment is made at two levels, the concept and the goal level, taking into account the difficulty level of the questions. To achieve the above, a rule-based intelligent component is used. To evaluate EX-COFALE, we implemented a course concerning fundamental aspects of radiation protection, which was used by a number of students in a nursing department and evaluated for usability of the e-learning system and educational content administration. The results are quite promising.