Essentially, there are two situations where interrogation might take place during a Dungeons & Dragons adventure: when the heroes are captured, or when the heroes capture an enemy. Both situations turn the game from a battle of might to a battle of wits; the captor seeks to learn precious information about a foe, and the captive seeks to delay, mislead or otherwise prevent the captor from obtaining it.
Some Dungeon Masters (DMs) may be inclined to resolve whether or not a captured foe shares information based on a single intimidate skill check. Others may opt toward structuring an interrogation as a fourth edition skill challenge, with the number of skill check successes dictating how much information is shared. A handful of DMs may decide to remove the dice completely from the equation, and allow the quality of the role-playing to decide how much information is gleaned by the captor.
Regardless of the mechanics behind determining the success of an interrogation in a D&D game, the process normally includes at least some role-playing – but what types of questions should be asked, and how should they be asked to maximize the chances of a truthful answer?