Tale of Jiraiya the Gallant

Titled Master's Prophecy and Vengeance in the anime, this Part II arc chronicles Jiraiya's investigation into Pain. It runs across volumes 40 to 42, covering manga chapters 368 to 383 and anime episodes 127 to 133 of Naruto: Shippuden. The Itachi Pursuit Mission precedes it, and the Fated Battle Between Brothers comes next.

Jiraiya tells Tsunade he intends to gather intelligence on the Akatsuki at its likeliest source, the hidden village of Amegakure. He slips inside but is detected almost at once by Pain. Questioning locals, he learns their new ruler single-handedly toppled Hanzo, the village's former master. Sensing danger, Jiraiya has the toad Gerotora hide the key to Naruto's seal within the boy should he fail to return, suspecting Madara Uchiha lay behind the old Nine-Tails attack on Konoha.

Konan strikes first, and after fighting her to a standstill Jiraiya recounts his history with her, Yahiko, and Nagato. Pain then arrives and lays out the Akatsuki's aim to forge a weapon capable of leveling whole nations, frightening the world into lasting peace. Grasping the scale of his foe, Jiraiya raises a barrier and enters Sage Mode with the aid of the toad elders Fukasaku and Shima. Together the three crush a trio of Pain's bodies with a powerful genjutsu.

The remaining Paths converge, and one severs Jiraiya's arm. Studying the corpses, he uncovers the terrible truth that every body once belonged to a ninja he knew, including his old student Yahiko. His throat is crushed before he can relay the discovery, and the Six Paths impale him together.

Clinging to life through sheer will, Jiraiya scrawls a coded message on Fukasaku's back, resolving that Naruto is the child of prophecy who must choose his own path. A final blow sends him drifting into the water, and as he sinks he settles on a title for his next book, The Tale of Naruto Uzumaki, deciding it has a pleasant ring. Fukasaku escapes with the vital clue, while Pain concludes his enemy is dead.