The episode starts with Rupert cleaning out his room, choosing some things to be stored in the attic and others to go in the trash. He finds his favorite toy from childhood — a squeeze dog named Mr. Squeezer — and plans to put him in the attic, but the boxes get mixed up, causing what he meant to go to the attic to be taken out with the trash.
When Rupert goes searching for his lost toy at the garbage dump, he discovers that old toys that get thrown away get taken to a Magical Land called Toyland — a paradise for toys where they never have to worry about being mistreated by owners. Life is perfect here... or is it?
It soon becomes clear to Rupert that life in this so-called paradise isn't as happy as everyone claims it is, and that their leader, a toy soldier named Colonel Tinker, rules his kingdom with an iron fist, and he hates nothing more than claims that any owners actually love or care about toys. Rupert's refusal to go along with the system gets him thrown in prison. Will he be able to escape and improve life for all the toys trapped in this place of ruin and despair? Does this plot sound familiar?
This film... er, episode provides examples of:
- A Boy and His X: A boy and his living toy dog.
- Actually, I Am Him: Rupert has to be pretend to be a toy at first, but after everyone gets confused when he keeps insisting Mr. Squeezer's owner wants him back, he finally confesses, "I'm his owner."
- After-Action Villain Analysis: After the battle, Rupert explains to the other toys why Colonel Tinker acted the way he did.
- The Alcatraz: Toyland (this is easy when your prison is a Magical Land with only one portal in and out).
- Alternate Character Interpretation: In-Universe — After the Colonel is defeated, the other toys conclude "You just wanted to own us!", that he became one of the evil owners he's always warned them about. Rupert disagrees, believing the Colonel didn't want anyone to leave because he didn't want to be abandoned.
- And Your Little Dog, Too!: Almost said ver batim by Colonel Tinker.
- Armor-Piercing Response:Colonel Tinker: Toyland is the land of freedom!Rupert: Well, if this really is the land of freedom, I should have the freedom to leave if I want to.
- Because You Were Nice to Me: Colonel Tinker is moved enough by Rupert saving him in the end to change his ways.
- Character Witness: Rupert helps several toys when he first arrives in Toyland. They later try to vouch for him and encourage everyone to trust him.
- Crapsaccharine World: Sunnyside D... er, Toyland — allegedly paradise, actually a prison.
- Dark and Troubled Past: It's best not to imagine what life was like for a toy who once belonged to Freddie and Ferdie Fox...
- Down in the Dumps: Rupert's adventure starts here (actually, since the Toyland portal is there, he would have had to come back that way, too, at the end...).
- Easily Forgiven: Rupert doesn't hesitate for a second to save Colonel Tinker from the mob of toys, despite everything the latter put him through.
- The Ending Changes Everything: In-Universe. Colonel Tinker casually drops the names "Freddie and Ferdie," causing Rupert to realize Freddie and Ferdie Fox were his owners. This immediately makes Rupert see everything he's done in a whole new light.
- Evil Cannot Comprehend Good: Colonel Tinker literally can't comprehend that any owner could be good to toys, nor can he believe it when Rupert saves him when all the toys turn on him.
- Extreme Doormat: All the toys are thrilled to have an owner to play with again. Rupert's too accommodating to tell any of them No even when it becomes way too much for him.
- False Utopia: Toyland again.
- Fantastic Racism: Colonel Tinker hates Rupert for being an Owner and tries to encourage all other toys to think the same.
- Fate Worse than Death: Colonel Tinker says he would rather be made into a soup can than go back to Freddie and Ferdie.
- For Want Of A Nail: None of this would have happened, and Colonel Tinker would still be keeping all toys under his thumb in Toyland, if Rupert's dad hadn't taken the wrong box to the curb.
- Freudian Excuse: Colonel Tinker used to belong to Freddie and Ferdie Fox. Their mistreatment of him made him hate all owners, and being abandoned made him desperate to prevent any of the other toys from leaving him.
- Hates Being Alone: Colonel Tinker forbade anyone to leave Toyland so he wouldn't be alone.
- Heel–Face Turn: Colonel Tinker apologizes to Rupert, realizes he was wrong about all owners, and becomes just as anxious as everyone else to leave Toyland and find a nice owner.
- Implicit Prison: Toyland again.
- Joker Jury: The villain — seemingly filling the roles of judge, jury, and prosecutor — puts Rupert on trial. Given the Fantastic Racism of the setting, the verdict is pretty much done before the trial even begins.
- Love Redeems: In the end, Rupert adopts the Colonel as his own toy.
- My Master, Right or Wrong: The other toy soldiers obey Colonel Tinker without question, even after one of them agrees with Rupert that he'd prefer to have a new owner rather than remain trapped here.
- Not Afraid of You Anymore: The toys gang up on Colonel Tinker after Rupert defeats him. Unusually for the trope, Rupert believes they go too far...
- O.O.C. Is Serious Business: While sitting in prison for the crime of simply being an owner, All-Loving Hero Rupert actually thinks, "If I were my right size, I'd show Colonel Tinker a thing or two." Of course, he admits he couldn't actually do that, but still, hearing Rupert Bear fantasize about getting back at one of his enemies, however briefly, is jarring.
- Pals with Jesus: Rupert's able to use his connection with Santa Claus to find new homes for all the toys.
- Prized Possession Giveaway: In the end, Andy... oops, Rupert decides to give his favorite childhood toy Mr. Squeezer to Bonnie... sorry, Toby.
- Save the Villain: Rupert returns the Colonel's key after the other toys take it, which would have left him unable to move or talk.
- Shrink Ray: The portal to Toyland shrinks giant toys (or boys disguising themselves as toys) so they can fit through.
- Something Only They Would Say: Possessive pronouns are forbidden in Toyland. Rupert first tips off the toys that he's not what he claims to be when he uses the phrase "my dog" — the toys would never say "my" or "your" anything.
- Unexpectedly Dark Episode: By Rupert standards.
- Vengeful Abandoned Toy: What else did you expect?
- Villains Want Mercy: Colonel Tinker is on his knees begging when the other toys overpower him.
- Where Is Your X Now?: No, seriously.Colonel Tinker: Where's your owner now?Rupert: I'm right here!
- You Meddling Kids:Colonel Tinker: It's that meddling owner...
- Zerg Rush: The toys unite against Colonel Tinker in the climax. Rupert stops them from hurting him.
