Season: 2

As Team Kakashi continues their search for Sasuke, Naruto suddenly collapses due to his previous fight with Orochimaru. As Naruto wakes up, Sai begins to reveal more about his brother, but Orochimaru suddenly attacks them. Sakura and Yamato come to Naruto's aid against Orochimaru, while Sai continues the search. Just as Sai finds Sasuke, Yamato finds Sai's bingo book with Sasuke listed as a target for assassination.

Kabuto fights Team Kakashi and frees Sai. However, Sai, who intends to learn more about his bond with his brother through Naruto's bond with Sasuke, betrays him. Captured, Kabuto gives a vague description of Sasuke's location to the team. Leaving Yamato's wood clone to watch over Kabuto, Team Kakashi enters Orochimaru's hideout and splits up to find Sasuke.

Yamato and the team enter Sai's room and confront him while Kabuto makes his way there as well. Sai tells Team Kakashi that not only was he to help with Konoha's destruction but also act as a spy against Orochimaru. Yamato reveals the secret of "Root"- its members were trained like Kirigakure's students in that they had to kill their friends so as to eliminate their emotions. Sakura returns Sai's book to him, remarking that he still has emotions because he treasures it. Sai then tells the group about his bond with his brother. Finally the team decides what to do about Sai's betrayal outside the lair. In doing so, Naruto tells the group about his own bonds and about how far he's willing to go to bring Sasuke back.

Sai receives a chilling glare from Sasuke's Sharingan that frightens him. Sai gives Orochimaru a bundle with information about Konoha's ANBU. Yamato gives Sakura and Naruto seeds with his chakra that enables him to track them inside the lair, and reveals that he was able to track Sai because he put a seed in Sai's clothing and food during the visit to the hot springs. Kabuto locks Sai in a room, and the boy summons a bingo book from scrolls he carries. Yamato uses a jutsu to open a tunnel into Orochimaru's hideout, and he, Naruto and Sakura travel to Sai's room undetected.