Clinical dentistry is learnt by the chairside through direct personal interaction between the patient and the clinical student. Patient interviewing, clinical examination and relevant investigations help the student clinician to arrive at a probable diagnosis so that he may assign a prognosis before charting out a tentative management plan. The importance of history taking in clinical learning cannot be over-emphasised. Both long-case examination and short-case examination try to assess two different aspects of clinical competence in arriving at a clinical diagnosis. Long-case is all about the detailed assessment of an important dental health condition after a comprehensive clinical examination. Short-case tries to test the skill of spot diagnosis and the ability to differentiate between similar clinical presentations. This chapter describes the importance of patient assessment and the important aspects to be observed whilst conducting a long case assessment as well as a short case assessment.