In the scenario of an objective structured clinical examination (OSCE) station, the proficient candidate will be expected to elicit information from the role-player or an actor, depicting the role of a simulated patient or trainee. Appropriate information is gathered using a combination of mainly open and some closed questions. History taking is a core skill which is usually included during every examination. Though the candidates are expected to acquire a high-grade scoring for such kinds of stations, unexpectedly, the marks for these types of stations remain consistently low. It is important for the candidate to excel in the technique of taking a comprehensive history, not only of the presenting complaint but also all the relevant past histories, including medical history, surgical history, treatment history, and obstetric history. Medication history (including the history of taking alcohol, smoking, and recreational drug use) needs to be taken. Social history and family history may also be important especially in some scenarios. The candidate must follow a logical approach while taking history and not forget any of the components of history taking. This chapter discusses 5 OSCE stations related to information gathering with different scenarios.