As Naruto continues searching for Sasuke with Sai, he collapses, due to his body having not recovered after entering his four-tailed form earlier. As Naruto falls unconscious, Sai carries him to the side. Sakura and Yamato continue searching each rooms, with Sakura getting impatient as they find themselves unable to locate Sasuke. Yamato warns Sakura not to rush in blindly, reminding her that they are in Orochimaru's lair and that there may be traps in place. Up on the surface, the Yamato wood clone continues to watch over Kabuto, who claims that the only map of the hideout is in his mind. Yamato's wood clone refuses to take Kabuto back to the hideout, unaware that the latter has prepared a Chakra Scalpel behind his back.
As Naruto regains consciousness, Sai tells him that Naruto reminds him of his adoptive brother. Sai recalls his memories with his brother and finally remembers what he wanted to draw, and quickly paints a picture of his brother and him smiling and holding hands. He tells Naruto that this was their dream, and that Naruto reminds him of his brother. Their conversation is interrupted by Orochimaru, who stumbles onto them while walking down a corridor. He uses his Hidden Shadow Snake Hands technique to attack them, but the two evade. Naruto tells Sai to rescue Sasuke while he handles Orochimaru. As Sai sets off, Naruto prepares to fight the Sannin, and uses Shadow Clone Technique. Naruto's infused chakra activates the tracking seed he had swallowed, and Yamato is signalled to the crisis. With his shadow clones, Naruto attempts to fight off Orochimaru, who uses his snakes and swords to dispel the shadow clones; Naruto hit a snake with Rasengan but finds himself caught by another snake. Orochimaru wonders whether this is the strongest Naruto can be; Naruto considers tapping into the Nine-Tails' power but remembers Yamato's warning, and decides against it, not wanting to risk losing control and hurting one of his teammates. Orochimaru decides to kill Naruto, but his attack is blocked by Yamato's Wood Release.
Sai, who theorises that Naruto's bout with Orochimaru should not only take time but summon Sakura and Yamato as well, takes the opportunity to use his Super Beast Imitating Drawing technique to create several ink rats to find Sasuke. Orochimaru senses Sai and spares Team Kakashi's life for the time being, asking them to repay him by killing off more Akatsuki members. Sakura asks where Sai is, and Naruto tells him that Sai went off looking for Sasuke. Sakura notices that Sai left his backpack and she smiles as she realises that he finished his picture book. Yamato finds a Bingo Book among Sai's belongings, surprised that he would even have such a thing in his possession. He explains to the duo that the Bingo Book has a list of individuals who are meant to be assassinated, and that if Sai has the book, then he must be on an assassination mission. Yamato, Sakura and Naruto are then shocked to see Sasuke's face inside the Bingo Book, and realise that Sai's true mission may be assassinating Sasuke. Meanwhile, one of his Sai's rats locates Sasuke's room and Sai opens the door, seeing Sasuke lying on his side with his Uchiha Clan symbol facing the door.