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Where in the U.S.A. is Carmen Sandiego? is an MS-DOS program and will require the proper system or a DOS emulator, such as DOSBox, to run properly.

The goal of the game is to track Carmen's henchmen across the U.S.A., arrest them, and recover the goods that he or she has stolen. To do this, the player must gather clues from witnesses about the suspect as well as the suspect's next location. Each new location allows the player to gather three clues, though the player may continue to the next location before interviewing all three witnesses. After a set number of visited locations, based on the player's ranking, the player will encounter the henchman. If the player has found enough clues about the suspect to issue a warrant and finds the suspect before the given time limit is reached, the player will capture the thief and the ranking will increase. If the warrant is issued for the wrong henchman or a warrant is not issued at all, the henchman will get away and the player's ranking will not change. After a certain number of successful cases, the player will eventually get a case that involves Carmen Sandiego herself.

Though the game does not track real time, each action will take a certain number of hours to complete. At higher rankings, the player must balance clue gathering with time management in order to catch up with the henchman in the given time frame.