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Naruto jolts awake from a bad dream in which Sakura and every woman he knows, wrapped in towels, closes in to thrash him for spying. Realizing Sai has vanished, he heads outside and meets Yamato, who says Sai is already out and asks Naruto to gather him and Sakura so the squad can begin its mission. Sakura finds Sai sketching and is startled that someone so cold could hold such talent. When she asks the title of his piece, he says he never names his work, and though she explains that artists usually draw titles from the feelings behind a piece, Sai admits he has made thousands of drawings yet labels none because he feels nothing.

Overhearing, Naruto sneers that a heartless type like Sai naturally lacks emotion and dismisses the artwork as unremarkable, prompting Sai to counter with a crude jab about Naruto's anatomy that leaves Sakura giggling and Naruto red-faced. Sai tells them to go ahead while he packs, and as Sakura helps she spots a picture book. He admits he drew it but refuses to let her read it, explaining it belonged to his older brother and is shown to no one. At the gate Yamato sees the team is still at odds, though Naruto and Sakura paste on smiles to smooth things over so the mission can proceed.

Bound for Kusagakure, Yamato veers off the road into the trees, wary that Sakura's intelligence could be an Akatsuki lure to seize Naruto. At nightfall he settles the group in a clearing and raises a wooden lodging with his Wood Release before briefing them. Because Orochimaru's informant expects Sasori, Yamato intends to wear the Hiruko puppet and pose as him, and he presses Sakura to supply Sasori's habits and manner to sell the ruse. He plans to make first contact and take the spy alive and unharmed, with Naruto, Sai, and Sakura held in reserve. Should a fight break out, he orders a buddy formation, pairing himself with Sakura and leaving Naruto and Sai together, an arrangement Naruto openly dislikes.