Rapunzel is having trouble picking a new lady-in-waiting. Eugene believes that it is because she still has not gotten over Cassandra, but she stubbornly denies this.
Two years prior Cassandra is annoyed at having to work for Rapunzel whose perky personality clashes with her more serious demeanor. Rapunzel wants to befriend her and seizes the opportunity when her parents announce that they are hosting the Contest of Crowns in which all seven kingdoms compete in a series of games. She forces Cassandra to be her partner and she reluctantly obliges. Rapunzel's methods turn out to be disastrous, but after showing off her physical capabilities, Cassandra is offered to join her royal guard, by the Queen of Ingvarr, but she will have to win the final competition where only the top two teams are qualified. Rapunzel ends up ruining everything for her and Cassandra angrily scolds her. She has a change of heart after realizing that neither of them has had much of a history making friends.
Rapunzel and Cassandra manage to work their way back to the top until it is just them against the Princesses of Ingvarr. The Queen of Ingvarr reveals to Rapunzel Cassandra's goal, making her feel betrayed. When Cassandra argues that this is an important opportunity for her, Rapunzel agrees that they should focus on winning. They are tasked with grabbing a flag on the back of giant iron lion. After a fierce battle, Cassandra chooses to help Rapunzel over grabbing the flag, but in the process, their friendship blossoms. Back in the present, Rapunzel breaks down to Eugene that she is still thinking of Cassandra and will do anything to get her friend back.
At the ruins of the caravan, Cassandra finds a painting of her and Rapunzel and begins to feel guilty about her betrayal, then is approached by the Enchanted Girl who reveals that the moonstone is not at full power because when Rapunzel touched the black rocks, part of its protective energy went into her hair. Realizing that Rapunzel is still undermining her, Cassandra angrily rips the painting of her and her former friend, symbolizing the end of their friendship.
- Mandy Moore as Rapunzel
- Zachary Levi as Eugene Fitzherbert
- Eden Espinosa as Cassandra
- Clancy Brown as King Frederic
- Julie Bowen as Queen Arianna
- Susanne Blakeslee as Old Lady Crowley
- Jennifer Veal as Enchanted Girl
- Peter MacNicol as Nigel
- Gina Torres as Queen of Ingvarr
- Mary Elizabeth McGlynn as additional Voices
- The wreckage of the caravan appears in this episode.
- The names of the seven kingdoms are revealed. They are Corona, Koto, Neserdnia, Bayangor, Galcrest, Pittsford, and Ingvarr.
- It's revealed when Rapunzel first touched the Black Rocks in Tangled: Before Ever After, the Moonstone granted a part of its power to Rapunzel, causing her hair to become indestructible, unbreakable and protective to ensure she would be safe on her journey to the Dark Kingdom and reunite with the opal. It also explains why Rapunzel can no longer do the Sun-Drop's Healing Incantation, but can now do the Moonstone's Reverse Incantation.
- When Rapunzel is playing with the oysters at the end of forks, she is imitating the famous fork dance scene from Charlie Chaplin's The Gold Rush.
- One of the events at the Contest of Crowns is animal calling. This is of course a nod to Disney's famous trope of princesses being able to call animals to their whim.
- The trophy of the contest indicates Queen Arianna and Willow were princesses of one of the seven kingdoms.
- This episode also happens to borrow its title from the premiere episode of Jim Henson's Fraggle Rock.