Air date: October 4th, 2013
One day, Bill and Ben encounter a fast engine, Connor to be precise, racing past them. Annoyed by the engine flying past them, they approach Thomas who tries to tell them that Connor is actually friendly. Ignoring Thomas's advice, Bill and Ben deem Connor to be too haughty for his own good and after seeing him race by a few times too many, the twins decide to prank him.
Bill approaches Connor at a signal and challenges him to a race, to which, the streamlined engine accepts. However, despite going as fast as he can and arriving at Ulfstead Castle, as per Bill's conditions for victory, he sees another engine who looks like Bill (actually Ben) and thinks "Bill" won. "Bill" taunts Connor over his loss and offers a rematch. Accepting it, Connor tries to go faster to outrun his opponent, but nearly crashes into Henry.
Connor is relieved to have narrowly avoided an accident, but soon sees that a nearby Sir Topham Hatt witnessed everything. As Sir Topham Hatt reprimands Connor for overrunning the red signal, Bill and Ben arrive to check up on Connor, causing the streamlined engine to realize the two twins tricked him. Furious at the twin engines for their trickery, Sir Topham Hatt sends Bill to the Steamworks to get a new paint job to ensure everyone can tell them apart.
Some time later, Ben sees Bill in a dark blue paint job, but Bill is not happy about it; everyone can now see who is who, not helped by the Steamworks crew being forewarned of Bill's antics and stopping him from weaselling his way out. However, Ben sneaks to the Steamworks and tricks Kevin into repainting him in the same colors as Bill.
Later, Bill and Ben see Connor again and Bill offers Connor to race him once more. Connor, who got word of Bill's repaint while unaware of what happened to Ben, accepts Bill's challenge. Unbeknownst to him, however, Bill cockily stays behind for a while, because he has ensured the streamlined engine has fallen for his and his twin's prank hook, line, and sinker again...
Tropes featured in the episode:
- An Aesop: Don't judge someone until you get to know them more.
- Bratty Half Pints: Bill and Ben are once again young and rather obnoxious twins who plan to trick Connor.
- Continuity Nod: Bill and Ben's trick on Connor shares some similarities to their trick on BoCo in "The Diseasel".
- Ignored Epiphany: Subverting the usual formula of the modern seasons, not only do Bill and Ben avoid punishment, they fail to even learn An Aesop and continue antagonizing Connor at the end of the episode.
- Karma Houdini: Though the Fat Controller calls them out for their prank like he did Connor, they manage to escape his intended punishment through trickery.
- Mythology Gag: Bill and Ben's race prank is very similar to one they pulled in the magazine story "Diesel's Race".
- Twin Switch: Bill and Ben pull this off by pretending that Connor is racing one of them only for him to believe that Bill beat him in the race although it was Ben who was standing near a platform at Ulfstead Castle. They've done this to him again in the ending after the twins were repainted blue.
- What the Hell, Hero?: The Fat Controller scolds Connor for passing a red signal and almost crashing into Henry. When he discovers the twins' involvement he expresses his lack of surprise and attempts to punish them too.
- Wrong Genre Savvy: After meeting Connor, the twins are immediately convinced he must be another pompous fast running engine who needs to be brought down to earth. As Thomas tries to point out, Connor is cocky, but is not a Jerkass.
