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We all know that Itachi had the left eye of Shisui which had the Kotoamatsukami. This was planted as the eye of one the crows of Itachi and the crow was planted inside Naruto, to counter Sasuke's Mangekyō, if ever, he turned against the village.

My question is, when did Itachi plant his crow inside Naruto and how did he do that?! Did he inject it inside Naruto, or planted it using Genjutsu, or something like that?

2 Answers 2

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Itachi stores the crow inside Naruto in chapter 403, during the Itachi Pursuit arc.
Itachi used a shadow clone to talk to Naruto, who wasn't willing to listen. As such, Itachi was forced to use a Genjutsu in order to make him listen.

He uses a Genjutsu as a distraction:
Itachi talking to Naruto

And then the crow is stored (physically, I think) inside of Naruto:
The crow entering Naruto

This is corroborated by this Naruto Wiki page.

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Itachi gave Shisui's eye to Naruto during the Itachi Pursuit arc. This eye was stuffed in the form of a crow, when Naruto was under Itachi's genjutsu.

See below image from Chapter 403, when Naruto is sitting in his room and having a flashback about his encounter with Itachi.

Itachi stuffing crow in Naruto's mouth

Background Eight Konoha shinobi went on a mission to find, and if possible capture, Itachi, since they hoped it would give some clues to Sasuke's whereabouts. At the same time, Sasuke with his Team Taka started moving to Itachi's hideout because he wanted to kill Itachi. Itachi knew his end was near, and it was part of his plan to die at Sasuke's hands.

Before he died, he wanted to talk to Naruto, presumably because he was still worried about what Sasuke would do after his death. He sent a shadow clone to talk to Naruto. This clone encountered one of the thousands of shadow clones that Naruto previously created to search for Sasuke.

Naruto was angered on seeing Itachi and unwilling to listen to anything Itachi had to say, so Itachi was forced to cast a genjutsu to make him listen. On hearing Naruto's determination to save Sasuke at all costs, Itachi decided to give him Shisui's eye, which would help him in case he had to take Sasuke back by force.

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