Peddlers Escort Mission

This arc of the original Naruto anime runs from episode 187 to 191. It sends Naruto out on an escort job to the Land of Vegetables and gradually reveals that the plain merchant caravan hides a far higher-stakes protection detail. In the broadcast order it comes after several standalone missions and leads toward the Matchmaking and Lady Daimyo missions and the Third Great Beast Arc.

Thrilled to draw a real assignment, Naruto joins Hinata and Choji to guard traders bound for the Land of Vegetables. When mysterious ninja begin picking at the group, the team splits for safety, and a dead merchant turns up dressed as a shinobi, tipping Naruto off that the attackers are hunting one specific person. The truth surfaces: the peddler Shun is really Princess Haruna, heir to the Vegetables throne, and two of her companions are her personal bodyguards, who disguised the real job as a cheap escort because a rebel band called the Janin had killed the daimyo and left them short on funds.

Naruto is furious to learn Haruna used innocent traders as bait, though he later hears how a bleak childhood spent far from home stripped away her faith in others. The pursuers, a trio of brothers with distinct techniques, attack in turn. Yurinojo, Naruto, and Choji drain one brother's water jutsu by luring him into a dry canyon, and Hinata turns another's magnetic sand against him with Gentle Fist.

The eldest brother, Renga, corners Naruto and Haruna with ice disks that shrug off every strike, until Naruto reflects a sunbeam off his forehead protector to bring him down. Overhearing Renga's plan to betray his own siblings, and learning that her father had surrendered her as a hostage yet loathed himself for it, Haruna rethinks her cynicism and spares Renga rather than take revenge. Crowned daimyo, she pledges to rule with compassion and asks Naruto to serve as her advisor, but he declines, still set on saving Sasuke.