Naruto Shippūden: Season 20, Episode 490

20 - 490: Shikamaru's Story, A Cloud Drifting in the Silent Dark, Part 2: Dark Clouds

After the Great War, many missing and Rogue Ninja made their way into the Land of Silence. Sai, who has infiltrated the region to investigate, sends a cryptic message back to the Leaf. Shikamaru, determined to find out what's happening, heads for the Land of Silence with two members of the ANBU, Soku and Ro. However, they must first get past a heavily guarded checkpoint.