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The Changeling: All the scenes of Nomad with crewmen on the Enterprise; if it wasn't space happy, and a planet killer, could a sentient alien probe join a starship crew? Like Illea, could something like her V'Ger made clone become a member of your crew? I mean you don't want something as powerful as Nomad, but could some sentient piece of alien tech become a member of Starfleet? Before you answer, remember: technically, Data joined Starfleet as equipment, and was declared a lifeform after YEARS of service.
Well... That brings up the question of whether there's a 'prove you're not a tricorder' test for admission to Starfleet. Or rather, given that Data could walk into an office and say, "I would like to join Starfleet," he probably passed that test in the Academy's eyes already.