"Following the Master's Shadow" (師の影を追って, Shi no Kage o Otte) is episode 153 of the Naruto: Shippūden anime.
Naruto leaves Tsunade's office as the Great Sage Toad Fukasaku muses how he hopes Naruto is the Child of the Prophecy. He reveals that before Jiraiya died, he managed to capture one of the Ame-nin, and that Jiraiya also managed to kill one of Pain's six bodies, which Fukasaku has in his possession. After giving the corpse to Tsunade, the Hokage orders Shizune to prep an autopsy unit. Fukasaku also has a picture of his back taken, asking the Hokage to decipher the clue and notify him, as well as to notify Naruto that he can always be reached at Mount Myōboku.
On his walk home, Naruto smiles as he sees an Icha Icha poster and remembers how Jiraiya would always peek at nude women, citing it as research for his books, and remembers his his first journey with Jiraiya. He encounters Iruka, who claims that the village is talking about him and offers to catch up over at Ramen Ichiraku, willing to treat him; however, Naruto refuses, wishing to be alone.
In her office, Tsunade tasks Shikamaru with deciphering the code as she leaves, crying as she remembers her last words with Jiraiya. At home, Naruto begins to cry and decides to take a walk late at night. After buying a popsicle, he sits down on a bench and allows the tears to stream from his face. Iruka walks up to him and consoles him as Naruto expresses how one of his wishes was to have Jiraiya witness his ascension to Hokage and how Jiraiya only knew the clueless Naruto during his time alive. Iruka reminds Naruto that he is a disciple of the Sannin and that Jiraiya always spoke highly of him, having considered him as a grandson, and that Naruto should continue to be the shinobi that he was so proud of. Iruka breaks the popsicle in two, taking one, akin to what Jiraiya used to do.
After Mitoku and Shiho of the Konoha Cryptanalysis Team notify Shikamaru that Jiraiya's code could only be broken by those closest to him, Shikamaru asks Tsunade and Kakashi, who cannot decipher it. Shikamaru then heads to Naruto's house, only to find the genin depressed. In order to snap him out of his funk, Shikamaru brings Naruto to the hospital to meet a pregnant Kurenai, and reveals that Asuma had entrusted him to be their child's teacher. He reminds Naruto that he knows what it feels like to have a teacher killed but that instead of crying about it, they should move on, and evolve from students to teachers, honoring the teachers they had themselves. Recalling a happy image of Jiraiya, Naruto smiles, and Shikamaru gives him Jiraiya's code to decipher.
- In Kakashi's flashback with Jiraiya, there were three minor mistakes:
|Role||Seiyū||English Voice Actor|
|Naruto Uzumaki||Junko Takeuchi||竹内 順子||Takeuchi Junko||Maile Flanagan|
|Sakura Haruno||Chie Nakamura||中村 千絵||Nakamura Chie||Kate Higgins|
|Kakashi Hatake||Kazuhiko Inoue||井上 和彦||Inoue Kazuhiko||Dave Wittenberg|
|Shikamaru Nara||Shotaro Morikubo||森久保 祥太郎||Morikubo Shōtarō||Tom Gibis|
|Fifth Hokage: Tsunade||Masako Katsuki||勝生 真沙子||Katsuki Masako||Debi Mae West|
|Shizune||Keiko Nemoto||根本 圭子||Nemoto Keiko||Megan Hollingshead|
|Fukasaku||Ikuo Nishikawa||西川 幾雄||Nishikawa Ikuo||Kirk Thornton|
|Iruka Umino||Toshihiko Seki||関 俊彦||Seki Toshihiko||Quinton Flynn|
|Jiraiya||Hochu Otsuka||大塚 芳忠||Ōtsuka Hōchū||David Lodge|
|Jiraiya (boyhood)||Toru Nara||奈良 徹||Nara Tōru||Brad MacDonald|
|Kurenai Yūhi||Rumi Ochiai||落合 るみ||Ochiai Rumi||Mary Elizabeth McGlynn|
|Shiho||Shiho Hisajima||久嶋 志帆||Hisajima Shiho||Laura Bailey|
|Cryptology team member||Daichi Endo||遠藤 大智||Endō Daichi||Michael Sorich|