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When reanimated Itachi fought against Naruto, he asked him what happened to Sasuke. Naruto proceeded to tell him about what Obito (at the time, Madara) said, and tells him the convince Sasuke to join the Akatsuki while taking revenge on Konoha for betraying his brother.

Itachi then looks surprised and says "Damn Madara, he knew about my secret mission after all".

However, given the fact that Itachi asked for his help in massacring the Uchiha, why is he so surprised? After all, he told him enough about it.

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    Maybe that time, he knew that Madara is Obito. So he actually telling the mission to Obito himself. – Nara Shikamaru May 29 '14 at 2:53
  • I don't think he did, and regardless, it doesn't really matter if he did or didn't know. (Fact that he said "damn Madara" even relatively later in the plot, when he was reanimated, means that he didn't know back then) – Madara Uchiha May 29 '14 at 6:31
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Itachi may have asked Madara's help but it was never explicitly said that he revealed the true reason behind his actions.

Itachi may have lied to Madara like he did to Sasuke that he massacred all uchiha to test his powers.

Itachi may be thinking that Madara was convinced with his reasoning, while Madara knew the true reason that he was doing all this by leaf village's orders.

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Maybe in the anime they made Itachi act surprised to not give away the plot. Or maybe he could be referring to another secret mission, in which it was Itachi's plan to help lead Sasuke to the right path, and yet Obito figured this out and used the darkness in Sasuke's heart to control him.

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