Leading a Stray! (Japanese: 迷子のホエルコ！The Stray Hoeruko!) is the 109th episode of the Diamond & Pearl series, and the 575th episode of the Pokémon anime. It first aired in Japan on January 8, 2009 and in the United States on June 6, 2009.
A Wailord blockage has trapped the boats in Canalave's harbor, and that means Dawn can't take a ferry to her next Contest. There's nothing to do but sit down for lunch, but a wild Luxio and its Pokémon accomplices steal the food! Pikachu and Piplup give chase, but run straight into Team Rocket. As always, Team Rocket tries to grab Pikachu, but Ash catches up with them and escapes into the sewer with his buddy. Piplup uses Whirlpool to toss Team Rocket, and now it's up to Ash to find his way back to his friends. As he wanders the sewers, he comes across the Luxio and its pals. They stole the food to feed a stranded Wailmer that somehow ended up in the sewer!
This Wailmer belongs to the Wailord group out in the harbor, and Ash offers to help Luxio get it back to its friends. He discovers there are many species of Pokémon living in the sewer, and Luxio is their leader; with all of their help, he can get Wailmer up a tall waterfall inside the sewer. Ash's idea is to make a giant ice ramp and push Wailmer up on a sled! Thanks to a last-minute assist from a Venonat, the plan works like a charm. As Wailmer swims even closer to freedom, Dawn and Brock find their way into the sewer and reunite with Ash. Things are looking up!
But one problem remains: a touchy Swampert mistakes Wailmer and the others for intruders in its territory, so it attacks. Ash's Grotle knocks it out and Wailmer swims out into the harbor... then evolves into a Wailord, too big to fit under the drawbridge up ahead! To force the drawbridge open, Pikachu, Luxio, and Pachirisu charge up the drawbridge controls, and Wailord swims through in time to avoid a second attack from Swampert. The new Wailord rejoins its pod and happily swims away as Ash thanks Luxio, then goes to eat his long-delayed lunch—he's earned it!
With Ash's sixth Gym Badge won, he and his friends prepare to head to Chocovine Town for Dawn's next Contest. However, the boats are unable to leave because the Canalave harbor is blocked by a school of Wailord. They have a picnic to wait out the blockade when a Luxio appears and steals food from the group. Piplup and Pikachu attempt to stop the Luxio, but a Whismur and Nidoran♂ help Luxio and manage to steal the food. Ash chases them into the sewer, where he finds many other Pokémon living in the underground drain and that Luxio is their leader. Dawn and Brock try to follow him, but a short battle with Team Rocket leaves the manhole cover sealed shut. Brock's Happiny tries to pull it off, but to no avail. Dawn then sends out her Mamoswine but it, as usual, doesn't listen to her. Dawn bribes Mamoswine with Poffins to open the manhole cover. It charges at Dawn and stomps on the ground, opening the manhole cover and sending Dawn and her Poffins into the air. Mamoswine eats the Poffins as they fall; Happiny catches Dawn. Down in the sewers, Piplup leads everyone to find Ash, although they often just miss each other.
Ash keeps following Luxio until he sees a Wailmer stranded on a walkway within the sewers, too tired to move. He sends out Buizel to hydrate Wailmer, and help it get into the water. He figures out that the Wailord blocking the harbor are probably worried about it, and decides to help it out. They head up the sewers toward the ocean, though they run into a drop on the way there. With a rope and the help of the other Pokémon, they are able to pull Wailmer over the first drop, but then are blocked by another huge drop. Ash enlists the help of all the Pokémon in the sewer, making an ice ramp up the drop and pushing Wailmer up on a sled. The plan works until the ramp crumbles half-way, and the Wailmer is struggling air-born. A Venonat asks Luxio to hit it up, which knocks Wailmer the rest of the way up the drop.
Dawn and Brock finally catch up with Ash, but when they are in sight of the exit, an angry Swampert comes after them, protecting its territory. Ash tries to reason with it, but it attacks instead. He is about to have Pikachu attack, but Brock points out that Electric attacks won't affect it, as it is part Ground-type. Ash calls out Grotle instead, attacking with Razor Leaf and sneaking by while Swampert is knocked out. Wailmer finally gets out of the sewers, but evolves right before he gets past a bridge. As a Wailord, he's much too big to fit under the bridge, but thankfully it's a drawbridge. Using Pikachu, Luxio and Pachirisu, they try to override the controls with electricity to raise the bridge, but they aren't enough alone. To make matters worse, Swampert has recovered and is coming after Wailord. Luxio lets out a cry, calling all the sewer Pokémon to come and join, despite not being Electric types, they can use Shock Wave. The bridge raises, Wailord gets out, and the wake of Wailord knocks Swampert back. With the Wailord school reunited, they leave for the open ocean and finally unblock the harbor. Dawn and her friends prepare to leave, but after Ash's stomach crumbles they decide to remain in Canalave for another night.