Shikamaru Hiden: A Cloud Drifting in Silent Darkness

Based on the novel Shikamaru Hiden: A Cloud Drifting in Silent Darkness, this Naruto: Shippuden arc covers episodes 489 to 493. Set after the Fourth Shinobi World War, it centers on Shikamaru's postwar life. Within the anime it follows the Sasuke Shinden arc and leads into the Konoha Hiden wedding story.

Restless after the war, Shikamaru shoulders paperwork for the Sixth Hokage while waiting for Naruto to claim the title one day. At a Shinobi Union summit he brushes off questions about a decline in shinobi support, and Temari, sensing a cover-up, slaps him. Konoha has quietly been tracking Gengo, ruler of the Land of Silence, who draws missing-nin to his cause. When Sai's squad is wiped out and Sai himself disappears, Kakashi sends Shikamaru along with two Anbu, Hinoko and Ro, to capture or eliminate the man.

Slipping into the walled town of Tobari, the trio gathers intelligence and learns that Gengo's rhetoric can bend even loyal shinobi to his side, helped by the scent of a local flower that dredges up painful memories. During a public address, Gengo parades a captured, entranced Sai and then turns his words on the infiltrators, converting Ro and Hinoko. Shikamaru resists by having Hinoko's chakra needles pierce his ears so the speech cannot reach him, but he is seized and imprisoned.

Ino, Choji, and Temari arrive to free him, and Temari's slap convinces Shikamaru he is not dreaming. As his friends battle the converted shinobi, Gengo corners him in a lightless room to smother his shadow techniques and sharpen his vulnerability. Yet by clinging to his faith in Naruto, Shikamaru shrugs off the manipulation, deduces that Gengo has used and discarded his own followers, and pins him long enough for Hinoko to silence his tongue.

With Gengo's voice neutralized, Konoha Anbu take him into custody and his scheme to destabilize the villages collapses. Released from the genjutsu, Sai, Ro, and Hinoko recover, and the mission closes on a lighter note as Shikamaru finally works up the nerve to ask Temari on a date, while Sai does the same with Ino.