"Dark Clouds" (暗雲, An'un) is episode 490 of the Naruto: Shippūden anime.
Someone tries pitting Sai against Konoha, questioning his position in Team 7 and pointing out Sasuke's return. Shikamaru, Hinoko, and Rō scout Sai's last known location, an inn. Shikamaru has disguised them as merchants to get past a checkpoint into a village, Tobari, while Hinoko argues it would be easier to kill the lookouts. Shikamaru points out doing so could reveal Konoha's involvement, and that Sai's team was killed. While Shikamaru talks of teamwork, Hinoko uses her chakra needles to kill a shinobi spying on them. She kills another one, who ends up falling on top of the vehicle they were using to pass as merchants. Shikamaru goes to the inn, where he manages to get information playing shōgi with a patron. He takes off before Hinoko can expose them, and chastises her for being so rash, while she refuses to botch a mission by being overly cautious. Rō tells Shikamaru she fears shinobi will be made obsolete in peace times, having not had the chance to prove her worth during the last war. The inn is interdicted, the shinobi Hinoko incapacitated outside being discovered, so everyone inn can only leave after having their identification verified. They escape with the help of Komori, who dislikes Tobari officials. Hinoko argues with Shikamaru about being allowed to act in the mission, and wonders she'd have more freedom in the Land of Silence. She storms off and talks with Komori in the inn, venting about her frustrations. As she returns, she overhears Rō and Shikamaru talking about silencing her if she truly wishes to desert Konoha. Komori tells her how to reach the Tobari checkpoint. Shikamaru and Rō follow her, but are interrupted by enemy shinobi. Hinoko reaches the checkpoint, where she announces her wish to join the Land of Silence, and incapacitates one of the guards to prove her skill. The guards notice the wound inflicted by her jutsu is the same on their killed comrades, and talk about a Konoha Anbu that spied on them a while back. Before they attack her, Komori shows up, vouching for her. Shikamaru and Rō arrive, and a fight ensues. Rō stops Shikamaru from harming Hinoko, saying they're misunderstanding her. Hinoko kills them both with her chakra needles, proving herself, and is brought inside. She puts Komori to sleep, and rejoins Shikamaru and Rō, who she only put in a death-like state for a while. Rō and Shikamaru suspected Komori when Rō faked a chakra presence in the inn and he reacted to it. The three successfully infiltrate Tobari.
|Shikamaru Nara||Shotaro Morikubo||森久保 祥太郎||Morikubo Shōtarō|
|Rō||Naomi Kusumi||楠見 尚己||Kusumi Naomi|
|Soku||Aya Saito||齋藤 綾||Saitō Aya|
|Gengo||Atsushi Ono||斧 アツシ||Ono Atsushi|
|Sai||Satoshi Hino||日野 聡||Hino Satoshi|
|Komori||Hirokazu Sekido||関戸 博一||Sekido Hirokazu|
|Merchant||Minoru Kawai||河合 みのる||Kawai Minoru|
|Enlightened Ones||Shogo Nakamura|