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A female spy, Hanare, from the Hidden Lock Village (Land of Key) is caught by ANBU pretending to be a musician. She is interrogated. However, the interrogation proves unsuccessful. Slowly, her past is revealed and so is her relationship with Kakashi. Team 7 spy on the two as they go around town, under the impression that the two are dating. After The Lock Village keeps a Leaf Village ninja hostage, they exchange Hanare for the ninja. It is then revealed that Hanare has a special ability, causing a large chase to occur. In the end, Kakashi lets Hanare free. The musician seen at the beginning entertaining Konoha ninja reminds Kakashi of Hanare which prompts the flashback.

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Naruto: Shippuden - Rotten Tomatoes

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Another error Funimation will probably never fix: Naruto Shippuden season 1 and 2 have been uploaded stretched sideways to fit a 16:9 image from a 4:3 source (comparison attached). : r/funimation

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Naruto: Shippuden - Rotten Tomatoes