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 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 a painting of her and her former friend.
- Princess Rapunzel
- Eugene Fitzherbert
- Captain of the Royal Guards (flashback)
- King Frederic (flashback)
- Queen Arianna (flashback)
- Pete and Stan (flashback)
- Lance Strongbow
- Zhan Tiri
- Old Lady Crowley
- Big Nose
- Faith (vocal debut)
- This takes place mostly in the six months of the movie series premiere Before Ever After
- It is shown that, in her youth, Queen Arianna and her younger sister Willow had won the Conquest of the Crowns together.
- The way Rapunzel says I'm not giving up on her, when she is referring to her and Cassandra is similar to the way Varian said "You didn't give up on me, I'm not giving up on you" when he referred to him and Rapunzel in Rapunzel's Return.
- This is the episode of how Rapunzel and Cassandra became friends for the first time.
- The names of the seven kingdoms are revealed. They are Corona, Koto, Neserdnia, Bayangor, Galcrest, Pittsford and Ingvarr.
- The way Cassandra has a lot to learn about being a friend during the flashback of this episode is similar to Varian's conversation with Rapunzel about him wanting to become friends with her again by learning to each other trust again in the episode Rapunzel's Return.
- The way King Frederic is mad when he is looking at Eugene during a flashback of this episode is similar to the way Lance and Maximus are mad at Varian when they are looking at him in Rapunzel's Return.
- The way Helmut massages Eugene during a flashback of this episode is similar to the way the former appeared in Tangled: Before After Ever.
- The way Rapunzel won't leave Cassandra's bedroom during the flashback of this episode is going to be similar to the way King Frederic won't leave Eugene's bedroom in The King and Queen of Hearts.
- The way Rapunzel and Cassandra are finishing each other's sentences is similar to the way Kiera and Catalina finished each other's sentence in Who's Afraid of the Big, Bad Wolf?! and it is similar to the way Rapunzel and Varian finished each other's sentence in The Alchemist Returns.
- Corona Castle
- Throne Room (flashback)
Objects of Immense Power
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