It's another peaceful day on the island, but Sonic and Tails are in the midst of battling Eggman's newest creation, Vaccum Bot. Eggman declares that this invention will get Sonic out of his hair once and for all. Sonic makes a joke, and then tries to attack Vaccum Bot, but the force of Vaccum Bot gets Sonic out of his Homing Attack. Sonic makes a desperate effort to escape, but he is sucked into Vaccum Bot. Tails lets out a Big "NO!", and Eggman lets out a Big "YES!", and comments on victory being sweet. Suddenly, banging is heard from inside Vaccum Bot, as it stumbles before exploding, due to Sonic having attacked Vaccum Bot from the inside. Eggman dodges a piece of the now-destroyed robot. Tails says that he should have never doubted Sonic, and Eggman says that he should have never gotten his hopes up. Tails asks Eggman if he really thinks he could capture Sonic with a poorly-designed tin can, but Eggman replies that it's not easy to capture Sonic. Eggman retreats, and Sonic says that Eggman was right about one thing, claiming that it is impossible to capture Sonic, but Tails says that Eggman never said anything about catching Sonic being impossible, just not easy...for him. Sonic, sensing that Tails assumes he can catch him, smack-talks Tails, and Tails decides to make it interesting so that the audience will appreciate that. Tails says that the loser of the bet will have to sing a romantic song at Meh Burger Karaoke Night. Sonic accepts.
At Meh Burger, Sonic and Tails are eating with their team. Amy thinks that the bet is stupid, but Tails says that they are just doing it for fun. Amy says that it's going to end badly, because Sonic can get a little competitive, and when Sonic scoffs at that, Amy reminds Sonic of a time when he competed with Knuckles to see who could put the most hats on monkeys, and Sonic and Knuckles laugh. Tails says that it's a competition between friends, with him and Sonic describing themselves. They look intensely at each other.
Tails has just finished setting a trap for Sonic, and Sonic, thinking the trap is foolproof, gets past it, but suddenly, a door somehow opens in the sand, and Sonic falls through. Sonic escapes and traps Tails with the cage. Sonic insults Tails for not understanding the bet, and gives Tails a C-.
At Sonic's Shack, Sonic detects another obviously-easily-avoidable trap and skillfully jumps over the rope. Sonic lays in his hammock in triumph, but it is rigged too, as a hand grabs the hammock and flings Sonic into a slide and eventually Sonic falls into a cage. Tails then comments that the slingshot hammock would work despite its terrible name and goes to check on the cage. To his shock, he finds that it is empty, revealing that Sonic escaped again. Sonic continues to smack-talk Tails and gives Tails a C+.
However, a Flybot is spying on Sonic and Tails, as Eggman comments that the slingshot hammock is first-season. Eggman comments that Tails has been watching his practice runs. Eggman then comes up with the fact that if Tails caught Sonic, Eggman can use it to his advantage. Cubot asks Eggman on how he is going to do that. Eggman replies that he will steal Sonic from Tails while he is captured, although he does not like people doing the work for him.
Tails is lifting barrels, and Sonic and Knuckles show up. Tails then makes an excuse that he promised Zooey that he would stack the barrels, before asking Sonic to lend him a hand. Sonic at first accepts, but then he notices another strange catch. Sonic has Knuckles do it for Sonic, and Knuckles, being Knuckles, decides to do it, while Tails tries to persuade Knuckles away from it, but it is too late, and as the barrel is stacked, Knuckles is caught in a barrel. Sonic makes a pun and dashes off.
Sonic and Amy are walking together, and Sonic is talking to Amy about the pun he just made about a few seconds ago, although Amy is not amused. Tails is spying on them, though, and he presses a button, which causes some boulders attached to a signal device begin rolling toward them. Sonic and Amy jump, but the signal-attached boulders also have a homing device. After a few seconds, Sonic redirects a boulder, and Amy does an awesome jump over another boulder, but she ends up losing her hammer while doing that, Sonic jumps out of the way, leading the boulders to trap Amy. Sonic makes another pun, and Tails breaks his binoculars in anger.
Sonic dodges some bear traps that Tails had placed down in the mine. Tails has apparently repaired his binoculars, as he looks through them. Tails yells that he will not hold back anymore, and it is revealed that Sticks was caught in a bear trap, and Sticks praises Tails' traps.
At the frozen lake, Sonic meets up with Tails again, but Tails seems to have finally given up. Sonic tells Tails not to feel bad, and Tails tells Sonic to help himself to a chili dog. But it turns out that it has a spring, and the plate rolls into a track, which sets off some wind vanes, which activate a rope for a hammer to cause a bowling ball to roll down into a cannon, where it is finally launched onto the X on the ice, causing it to crack and leave Sonic unable to escape and struggle to stay on to not fall into the water. Tails declares victory, but Eggman appears, revealing that he tricked Tails into capturing Sonic; Tails did the work and Eggman got the rodent. Tails prepares for battle, but then realizes that the rest of Team Sonic is still trapped. He runs off while Eggman laughs in victory.
Tails frees Knuckles by pressing another button to break the barrel that Knuckles is trapped in, and after Knuckles comments that he had a dream where he showed up at school wearing pants, Tails tells Knuckles that Sonic is in danger. Tails reverses the boulders that Amy is caught in, and Amy angrily tells Tails that she told him this would go too far. Tails tells Amy that they got to save Sonic. Sticks somehow freed herself. Now with Team Sonic together again, Tails and company set off for the frozen lake.
Eggman has somehow deployed some Bee Bots to make Sonic's struggle to not fall much more harder. Eggman comments that Eggman has to build a freezer to hold Sonic the Hedgecicle in. Cubot gets the meaning of cicle wrong. Orbot suggests Hedgecube. Sonic's teammates show up to destroy the Bee Bots, with Amy destroying one, and Sticks knocking one away with the slingshot. Eggman scolds Orbot and Cubot for allowing Sonic's friends to show up. Tails destroys the final Bee Bot, but the blast from it causes the ice to break further, causing Sonic to scream and yell for help. Knuckles calls Sonic a "Hedgecube, and Eggman glares at Orbot. Knuckles lifts the ice, and Sonic tells Knuckles to throw him at Eggman as hard as he can. Knuckles obliges. As Eggman is flung away, Eggman declares that he almost had Sonic. Tails apologizes to Sonic, but Sonic says that he got over-competitive. The rest of the team comments that Tails trapped them too. Tails apologizes to them as well. Sonic says that there is one more thing.
At Meh Burger Karoke Night, Tails sings as the rest of Team Sonic watches, and Sonic decides the bet was a bad idea due to Tails' horrible singing, and the episode ends.
This episode provides examples of:
- Affectionate Gesture to the Head: Sonic does this to Tails in a rather insulting way after the former escapes the latter's traps.
- Be Careful What You Wish For: Sonic and Tails' bet was for the loser to sing a romantic song on karaoke night. At the end, listening to Tails's singing, Sonic realizes that was a terrible idea.
- Breaking the Fourth Wall: This exchange between Sonic and Tails:Tails: What say we make it interesting?
Sonic: I think the audience'll appreciate that.
- Continuity Nod: While carrying barrels, Tails claims that he's doing it for Zooey as a favor; this implies the two have continued to see each other after the end of "Tails' Crush", where Tails managed to win Zooey over with his heroics.
- Humiliating Wager: The entire impetus of the episode is Sonic and Tails' wager where the loser has to sing a romantic song at Meh Burger's Karaoke Night.
- Kansas City Shuffle: Tails' traps for Sonic. For example, he has a very obvious cage trap over a chili dog, but the real trap is a pitfall outside the cage.
- "Not Wearing Pants" Dream: Inverted, though not shown; when Tails frees and wakes a sleeping Knuckles from the former's barrel trap, Knuckles claims that he was having a dream where he came to school wearing pants.
- Road Runner vs. Coyote: Sonic acts as the Road Runner to Tails' Coyote.