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In 2267, Harry Mudd became stranded on the android's planet and found that the local inhabitants were willing to obey his will and serve him in all ways possible. While "Lord" Mudd initially enjoyed himself, he soon became weary of being stranded forever on the planet, and hatched a plan for escape. He sent Norman to capture a Federation starship so that he could leave and have the starship's crew replace him.
Norman managed to pose as a Starfleet sciences division crewman and boarded the USS Enterprise. Doctor McCoy was the first to have suspicions, as he noticed un-charcterisitic, "human" behaviour. Such as not smiling. After successfully taking control of the Enterprise, Norman brought the ship to planet Mudd to carry out Harry's plan. While he temporarily de-activated himself for the 2-week travel time.
Unfortunately for Harry, the plot ultimately failed when Captain James T. Kirk and Commander Spock were able to deduce that the androids were a hive mind and that Norman served as a control locus. In order to escape the planet, the Harry and the Enterprise crew were able to overload Norman's processors by performing a series of illogical acts. Norman and the other androids were later reprogrammed to make the planet inhabitable; Mudd was left as a example of Human failure-along with 500 copies of his nagging wife Stella Mudd as his parole officer. (TOS episode: "I, Mudd")
In the 24th century, a new version of Norman - dubbed Norman 2.0 - still served as the central controller on Mudd's world. Norman was eventually reprogrammed by the M-5 computer (which had escaped from Romulan captivity) to serve M-5 in its attempt to eliminate all enemies of the Federation. (Speculations - Strange New Worlds 8 short story: "Concurrence")