Imprisoned and separated from Toothless on Outcast Island, Hiccup finds himself and his dragon at Alvin's mercy. Alvin makes it clear that if Hiccup doesn't train dragons than Toothless's life is forfeit.
Tropes for this episode include
- Actually Pretty Funny: Savage laughs at Hiccup's "low-hanging fruit" line. After Alvin whacks him on the head, however, he retracts that statement quickly.
- Androcles' Lion: The dragons that Hiccup has befriended end up rescuing him and Toothless from the Outcasts in the climax, without any prompting from their riders.
- Awesome by Analysis: Gobber when examining the fake Night fury deduces that it came from Outcast Island since it's made partly from Loki Tree wood, which only grows on that particular island.
- An Offer You Can't Refuse: Subverted. Alvin tells Hiccup bluntly that if the boy doesn't train the dragons, then the Outcasts have no use for a Night Fury like Toothless. Before Hiccup is forced to train dragons, however, Alvin implements another gambit, where he pretends to toss Mildew into a cell and prepare to execute him.
- Badass in Distress: Hiccup and Toothless for most of this episode, at different occasions.
- Berserk Button: Hiccup hates being called "Stoick's little runt".
- Big Damn Heroes: The other dragons save Hiccup and Toothless in the climax, without any commands from their riders.
- Call-Back:
- The dragon calls from the previous episode lead to Hiccup and Toothless finding each other.
- Trader Johann helps the riders sneak onto Outcast Island and find out where Hiccup was imprisoned.
- Can't Kill You, Still Need You: When Toothless stops eating, Alvin tells the guards to keep the dragon alive since they need him as leverage against Hiccup.
- Chekhov's Gun: The dragon calls from the first part.
- Chekhov's Gunman: Trader Johann.
- Complexity Addiction: Alvin with his gambits. If not for Hiccup falling into his traps so easily, he wouldn't have succeeded by the end.
- Cruel Twist Ending: Mildew ends up being a Fake Defector, and he gives Alvin the dragon training that the Outcasts covet.
- Deadly Euphemism: If Hiccup doesn't train dragons for Alvin, none of the dragons are "of any use" to Alvin, especially Toothless.
- Defiant Captive: Hiccup and Toothless. The former is at his snarkiest and does everything he can to escape, at one point using his prosthetic leg to try and knock out a guard. Toothless stops eating and pretends to be sick to trick the guards into taking off his muzzle, escapes quickly, then spends the rest of the episode looking for Hiccup.
- Didn't Think This Through: Hiccup snarking at Alvin, trying to attack a guard with his prosthetic foot, and then charging at Alvin with Toothless in the climax. Heck, he runs on this trope for the entire episode except when he reluctantly frees Mildew.
- Enemy Mine: Mildew and Hiccup, to escape from the Outcast cells. Ends up subverted, since Mildew was an agent for Alvin during the temporary alliance.
- Fake Defector: Mildew. At first it seems he truly learns to appreciate dragons, but after being "recaptured" on Outcast Island he teaches Alvin what Hiccup taught him about dragon training.
- Gambit Roulette: Alvin was relying on the fact that Hiccup would surrender to the necessity of needing Mildew's mental map of Outcast Island to find Toothless, and that he would teach Dragon Training to the latter.
- Idiot Ball: Hiccup trying to attack Alvin when he's already rescued, flying with Toothless into an obvious trap.
- It's All My Fault: Hiccup blames himself for getting captured, with Toothless as a hostage.
- Nice Job Breaking It, Hero: Hiccup during most of this episode. First, he snarks advice for dragon training while touring the pits, which Alvin notes as making Hiccup even more invaluable, and then tries to attack Alvin in the climax.
- Oh, Crap!:
- Hiccup when he fails to knock out a prison guard with his prosthetic.
- Toothless when he finds Hiccup missing from his cell.
- Stoick when Alvin deliberately presses Hiccup's Berserk Button and calls him the former's "little runt".
- Open Mouth, Insert Foot: Hiccup due to his Deadpan Snarker moments not only reveals dragon training secrets to Alvin but also makes jokes that earn him some violent shoves.
- Playing Possum: Toothless does this while tied up, muzzled, and dangling from the Dragon Pit ceiling, closing his eyes and refusing any food or water. The guards, worried that he'll die, removes his muzzle to force-feed him. He proceeds to free himself, knock the guards out, and start searching for Hiccup.
- Shout-Out:
- Gobber and Stoick's analysis of the fake Night Fury hearkens to Batman's and Sherlock Holmes' deductions.
- This first season finale ends the same way as the Avatar: The Last Airbender second season finale — a minor villain and one of the heroes get thrown in prison together, where they seemingly bond, and the villain seems ready to join the hero's side, only to side with the main villain and betray the heroes, leading to The Bad Guy Wins (although, in Hiccup's case, they don't know it).
- This Is Gonna Suck: Gobber after Alvin presses Hiccup's Berserk Button in the climax.
- Wham Shot:
- Alvin undoing Mildew's bonds at the episode's resolution, revealing Mildew was a Fake Defector.
- Alvin bonding with the Whispering Death.
