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James T. Kirk is infamously known for (among many other things) having hacked his way through the Kobiyashi Maru test. However, I can't think of any other times we've seen him exhibit any extraordinary computing (let alone hacking) skills.

Are there other canonical examples of Kirk himself breaking into computer systems?

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    I think he just plays the fight music and scares them into submission. – Xantec Feb 27 '13 at 19:09
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    On a more serious note, in the deleted scenes of Star Trek (2009) Kirk wasn't the one who modified the test parameters. It was instead supposed to have been the Orion woman he was intimate with who did it for him. – Xantec Feb 27 '13 at 19:10
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    I think that you can chalk up another conquest for James Tiberius. He very likely slept with a programmer and got her to do it for him. – coleopterist Feb 27 '13 at 19:10
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    Not necessarily. He says he cheated and altered the test, but I don't believe it was ever established in prior canon that he was the one who actually carried out said programming. I go with @coleopterist, and imagine he probably did something similar in the "real" timeline too. – eidylon Feb 27 '13 at 19:17
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    Kirk would definitely use social engineering to achieve computer security related goals. He's not the sort to break a system through technical means. – dmckee Feb 27 '13 at 19:41
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Kirk is shown hacking the following computers and cyborgs, typically exploiting bugs in their programming in order to cause them to self-destruct:

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    Interesting how these wouldn't quite fit most expectations of one's imagination when thinking of "computer hacking". They're mostly examples of AIs being taken down by logical fallacies. I was sort of hoping to find another example more similar to his exploit of the Kobiyashi Maru (surely, he didn't do that just by talking to the computer) but I guess this is as close as we can expect to get, from an age where computer hacking wasn't nearly so much in mainstream media. – Iszi Feb 27 '13 at 21:00
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    In the Star Trek world where voice is a primary form of input instead of something like a keyboard, these exploits really are a future form of hacking. – Caimen Feb 27 '13 at 21:53
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    @Caimen Yup, the closest thing to computer programming we usually see in Star Trek is when people are making things on the holodeck. And it's all 'computer, create this', 'computer, make this behave in a certain way' and so on, all entirely verbal. – user1027 Feb 28 '13 at 1:15
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    @Keen Ah, but let's not forget Scotty in ST4. "Hello, computer." – Iszi Feb 28 '13 at 5:06
  • @Keen one exception would be the Binars. – Caimen Feb 28 '13 at 17:41

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