Shikamaru Hiden: A Cloud Drifting in Silent Darkness (Arc)

is an arc of the Naruto: Shippūden anime. It covers episodes 489 to 493. This arc is an anime adaptation of the Shikamaru Hiden: A Cloud Drifting in Silent Darkness novel from the Naruto Hiden series that focuses on Shikamaru's life after the Fourth Shinobi World War. In the anime, it takes place after the Sasuke Shinden: Book of Sunrise arc and is followed by the Konoha Hiden: The Perfect Day for a Wedding arc.

Summary
Shikamaru has been busy helping the Sixth Hokage with paperwork since the war but he is bored with his desk job and insists he is doing the work until Naruto becomes Hokage. After work, Shikamaru plays shogi with Ōnoki, whom he easily defeats, and goes to the forest to train. At Shinobi Union meeting in the Land of Iron, the village ambassadors each discuss the decline of shinobi assistance and Shikamaru simply replies the matter is being investigated, but Temari suspects he is hiding something and his refusal to answer her questions causes her to slap him in anger. After returning to Konohagakure, Shikamaru and Kakashi discuss their suspicions of the leader of the Land of Silence, Gengo recruiting missing-nin and how Konoha has been silently investigating. However, Sai's team has been killed and they are concerned for Sai's well-being. Kakashi asks Shikamaru to go to the Land of Silence to capture or assassinate Gengo, with the company of two Anbu, Hinoko and Rō, as teammates. Shikamaru visits the graves of his father and Asuma, where he is greeted by Kurenai and Mirai, who have come to visit Asuma's grave. He later meets with Ino and Chōji for dinner and the three discuss how much their lives have changed since their genin days. The next morning, he leaves to meet his comrades at the village gates, Shikamaru runs into Naruto, who is on his way to eat ramen for breakfast, and advises him to stay the way he is because he will become Hokage one day.

Once they arrive in the Land of Silence, Shikamaru decides that disguising themselves will help them get past the checkpoint of the village, Tobari. However, Hinoko believes killing the shinobi is easier and uses her Chakra Needle to kill two who were tailing them. They track Sai's last known location, which is an inn near the checkpoint. Shikamaru plays shogi with a villager to gain information on Gengo and the man's remarks about shinobi being disposable tools for citizens angers Hinoko, who fears shinobi will be eradicated during peaceful times. Hinoko desires to prove her worth and the inn is suddenly being raided by shinobi, Hinoko's earlier killing of their partners exposing them. Shikamaru, Hinoko and Rō are saved by a busboy named Komori who claims to hate Tobari. Hinoko contemplates defecting Konoha to prove herself, which strains her from Shikamaru and Rō, who warn her about the consequences of betraying her village. Later that night, Hinoko goes to the checkpoint and asks to join the Land of Silence. The guards doubt her trustworthiness but Komori reveals himself to be a follower of Tobari and he had spied on her to see her abilities for himself, and wants her to prove her loyalty. Hinoko easily defeats two guards before Shikamaru and Rō arrive to stop her. Shikamaru abruptly accuses Rō of betraying him as well but both are seemingly killed by Hinoko. Satisfied, Komori takes her into the village but she knocks him out and returns to let in Shikamaru and Rō, who had been placed under a temporary death state as part of a plan to gain entry.

Episodes