As our heroes are getting ready to head for Snowpoint City, Team Rocket makes a sudden grab for Ash's Pikachu. Our heroes fight back, and Team Rocket flees empty-handed while Pikachu ends up in the hands of "Wild" Officer Jenny and her Chatot partner. She was transferred to Sinnoh from Kanto, and she's on the trail of Team Rocket. In fact, she wants Ash and his friends to stand as decoys until Team Rocket returns. But when the chief of police catches Jenny luring the kids into another one of her crazy investigations, she gets a stern lecture.
With her plan foiled, Officer Jenny offers to take our heroes out to lunch instead. When they run into some crooks along the way, Jenny knocks them down with her set of bowling balls and Chatot uses Feather Dance to help apprehend them. As Jenny basks in the glow of a job well done, Team Rocket shows up to swipe Pikachu in a net. Officer Jenny jumps in front of Pikachu, and Team Rocket snags her Chatot by mistake! But Chatot has been Officer Jenny's pal and partner ever since she became a detective, and she won't let Team Rocket get away with this.
Team Rocket escapes and holes up in their hideout; they're hoping to give Chatot to the boss, but the talkative Pokémon is getting on their nerves. Staravia leads Officer Jenny and our heroes to the hideout, and Team Rocket tries to evade capture by jumping into their own giant bowling pin-shaped robot. No matter what attacks our heroes try, the robot refuses to be knocked down! But once Jenny's well-aimed bowling ball knocks over the robot, Chatot takes the opportunity to escape from Team Rocket. Team Rocket figures Jenny is out of bowling balls, but she has one weapon left: Chatot's Steel Wing! Chatot demolishes the robot, causing an explosion that sends Team Rocket sailing away. Now Officer Jenny and her Chatot can head to their next assignment in the Whirl Islands, and our heroes can finally head for Snowpoint City for Ash's next Gym battle!
On their way to Snowpoint City, Dawn admires her four Ribbons so much that she begins to walk away from Ash and Brock. She knows that she only needs one more Ribbon to enter the Sinnoh Grand Festival while Ash only needs two Badges to enter the Sinnoh League. Team Rocket, disguised as Jubilife TV, approaches Dawn to conduct an interview about her recent Contest win. The distraction allows Meowth to grab Pikachu with a mecha arm while Jessie covers the escape with a smoke bomb. As the smoke clears, Team Rocket takes off in their balloon before reciting their motto. They attempt to escape as Piplup fires Bubble Beam, freeing Pikachu. Pikachu fires Thunderbolt to destroy the balloon and sends Team Rocket blasting off early. Ash rushes to catch Pikachu, but a motorcycle speeds by and an Officer Jenny jumps off her cycle and catches the Pokémon in midair before landing back on her moving cycle and stopping, noting that Team Rocket got away.
Ash gets Pikachu back as Officer Jenny asks if he is Ash Ketchum from Pallet Town, which he confirms. Jenny places him under arrest, but only to help him. The group notices Jenny's more aggressive demeanor and her talking Chatot. Brock makes his usual advancements, but before Croagunk executes a Poison Jab, Jenny's Chatot beats Croagunk to it by pecking Brock down. Dawn checks her Pokédex as Jenny reveals she was transferred from Kanto and heard about Team Rocket setting up in Sinnoh. She requests Ash's help since he frequently encounters them. Ash mentions that they always want Pikachu, so Jenny checks Pikachu, noting nothing special. When she tugs on his ear, Pikachu has had enough of being man handled, and Chatot manages to quickly fly off before Pikachu shocks Jenny. Nonetheless, Ash agrees to help. Jenny has Ash and his friends wait in an open park while she watches from behind a tree. Dawn believes that she is leaving them open as bait to lure Team Rocket in. A pair of officers approach and pinpoints Ash Ketchum. Officer Jenny comes up and reintroduces herself, trying to keep her role secret. The chief does not fall for it and knows what Jenny is trying to do, further proved by the talking Chatot. He mentions that she has only been causing trouble since her transfer before taking off.
Jenny tries to push the topic off by offering the group lunch. It satisfies Ash and Brock, but Dawn is still suspicious of her motives. While they eat, the group notices a bunch of thieves fleeing a building across the street. Jenny races outside, strapping on a bowling glove and rolling a bowling ball at the thugs. She tosses two bowling balls and knocks down two thieves. One tries to grab another to flee, but Chatot puts them down with FeatherDance. The last thief runs around a corner, but Jenny tosses another ball, curving around the corner, and stopping him. Before he can get up, Jenny confronts the last one and intimidates him into surrendering, making him think that she saved a very strong bowling ball. As she slaps the cuffs on him, Ash and his friends realize that she did bluff, the media crowding around her and taking pictures.
Team Rocket returns, trying to swipe Pikachu with nets, but Pikachu dodges the swipes. Officer Jenny steps forward to block the swipes. Team Rocket snags something and flees without checking. Everyone thinks they got Pikachu, but the Electric Pokémon stands behind Ash. Jenny notices that Chatot is no longer on her shoulder. Jenny tries to pursue, but she trips on a rock, clearly upset at letting Chatot get caught. Ash summons Staravia to search. As they walk, Jenny discusses about how she first met Chatot. When she was pursuing a suspect, she knocked him down with her bowling ball, but he still managed to get up. A wild Chatot blocked his escape and used FeatherDance to put him down. Since then, Jenny and Chatot have worked cooperatively to take down criminals. Ash sympathizes with her bond to Chatot, similar to his bond with Pikachu.
While in their cabin, Team Rocket ponders over the net, thinking they got Pikachu. When they hear chatter, they know something is amiss and quickly remove the net, revealing Chatot. Meowth decides that sending Chatot to Giovanni would help give the boss a morale boost by asking the Pokémon loaded questions, boosting his confidence. While Staravia returns to the group and leads them to Team Rocket's location, Team Rocket quickly grows irritated at Chatot repeating lines, twisting them into insulting remarks. When they get to the cabin, Jenny volunteers to go in alone, but Ash and his friends insist on helping as well.
Chatot continues to annoy Team Rocket when Jenny rolls her bowling ball, breaking the door and walking inside, Ash and his friends busting in through windows. Team Rocket quickly grabs Chatot before retreating into another room. When Ash and his friends follow, they fall into a pit leading to an underground tunnel. Jenny reaches the end first, pulling Ash and his friends up as they confront a bowling pin mecha. The mecha fires bowling pin missiles, knocking everyone down. Jenny gets up and straps her glove on before rolling her bowling ball. It causes the mecha to tilt, but it quickly levels. Pikachu's spinning Iron Tail attack also fails to knock the mecha down. Piplup's Whirlpool almost causes it to fall, but the mecha deploys legs to stabilize it. Jenny sends another bowling ball speeding at one of the legs, knocking the mecha down. Inside, Meowth gets annoyed by Chatot and opens the cage. Chatot pecks everyone inside, causing Jessie to open the hatch and release Chatot back to Officer Jenny. The mecha gets back up as Jenny pulls the same line she used to bluff the criminal earlier. Team Rocket thinks she is really bluffing and charges. Instead of a bowling ball, Jenny sends Chatot forward with Steel Wing, breaking the mecha to pieces and causing it to explode, sending Team Rocket blasting off. She realizes too late that they would get away. At sunset, Ash and his friends thank Jenny for her help as she mentions her transfer to the Whirl Islands. The group continues on to Snowpoint City.