While doing her handmaid duties, Cassandra notices a poster for a tournament called the Challenge of the Brave, where all the kingdom's fiercest warriors compete. She starts training for the competition, while at the same time carrying out her duties as Rapunzel's lady-in-waiting. While walking through town she sees a thief stealing a purse from an old lady. Cassandra is ready to take him down, but just as she was about to do so, a royal guard comes in and catches the thief with ease, upsetting Cassandra. After her next training session, some children stand nearby and watch her completing an obstacle course with ease. She first thinks they are impressed by her skills only to find out they really are excited about Rapunzel, who has been standing behind her. Cassandra stays unnoticed by them which greatly hurts her. Rapunzel tells her friend how impressed she is and asks her why she has been training so hard. As Cassandra answers her question the princess immediately wants to take part in the competition telling her she wants to do it together. Fearing Rapunzel taking part would again overshadow her dreams and her hard work put towards accomplishing them, Cassandra lies to her by claiming that taking part is by invitation only.
At the arena Wreck Marauder, the most feared warrior arrives. The other competitors run away in fear as he comes along. Eugene sits on the stand and cheers excitedly for him. His blowing very loudly into a horn subsequently ends with him being sent to the top of the stand. Cassandra meanwhile trains her bow-and-arrow-skills at the competitor's section, only to overhear the other competitors making fun of her. Rapunzel comes along with her happy attitude. She hugs some competitors which result in her being liked by everyone again. Cassandra tells her that it is not the time or place for that. Cassandra brushes it off, saying she does not need luck and wants to talk the competitors down with trash talk, starting with a warrior who has just eaten some beef. She tells him it is not about the strongest breath, but sadly it does not have the effect Cassandra expected as his breath is really bad and he tells her to get back to her lady-in-waiting duties. Rapunzel is not sure about Cassandra's methods but tries it anyway. She fails and comments on another competitor's tattoos instead of robbing his confidence. As Wreck Marauder comes along Cassandra drags her friend away, but fails instead with Wreck trash-talking her. Rapunzel stands up for her friend, which results with Wreck laughing, leaving Cassandra feeling even worse. After finally dragging her away, Rapunzel leaves for the stands after hugging Cassandra and tapping her on the head.
The tournament starts and the announcer introduces the competitors: Razor Blade McDoom, a woman with sharp teeth, Wreck Marauder, and Cassandra. Rapunzel arrives at the top of the stands, taking her place next to Eugene. He tells her it is up there they can see everything while in reality, the arena is very far away. As they talk about Cassandra, Eugene tells Rapunzel that there is no need for an invitation to take part. Delighted, the princess decides to take part and immediately steps into the arena. Everyone cheers for her, making Cassandra feel disrespected. The first challenge is to dodge swinging hammers. The first contestant fails while the others making it through, Cassandra having trained for it, and Rapunzel succeeds by dancing around the hammers. Everyone cheers even louder for her, leaving Cassandra unseen again. Rapunzel over eagerly runs to Cassandra who does not seem too impressed by her friend's performance. She tells her it will be useless against Wreck in the last challenge, the Dead Man Circle.
The second challenge involves hitting a target with an arrow. Cassandra hits the bull's-eye with enormous skill and accuracy, And Rapunzel, after having trouble with the bow, succeeds by using a guitar as a bow. Wreck, on the other hand, breaks the whole target. Eugene in his joyfulness blows his horn again, having the same result as before: him landing on another stand again. Meanwhile, the next challenge has begun. The competitors are required to jump over an obstacle. Cassandra accomplishes this easily, Rapunzel jumps gracefully over it, the next one, who has a hook for a foot, fails because his hook gets stuck. As Wreck hops over the obstacle he falls down to the ground. The score now shows that Wreck is in first place, Cassandra second with Rapunzel slowly becoming a threat to her. Eugene has changed his Wreck flag to a Rapunzel flag. As Pascal blows the horn again, they get sent to another place. Another challenge before the Dead Man Circle revolves around lifting some rocks. Wreck has no problems, Cassandra is able to lift her lid triumphantly, but Rapunzel, having her hair, uses it as a rope in a pulley to lift a bigger set of rocks than her friend, making Cassandra's jealousy grow. Again the horn is blown, finally earning Eugene a VIP seat, which turns out to be a seat on a very important pig. The last challenge before the finals starts- trying to stay on a turning log swimming in water. Rapunzel wins as she does not wear shoes and happily jumps into the water after Cassandra, who is the second to last left other than Rapunzel, fell in. While she resumes to having fun with the other competitors, Cassandra gets even more angry as Rapunzel is now second place with herself being third. She even gets angry at the judge, claiming he does not know the rules because Rapunzel had no shoes like it is supposedly required. After that she openly asks the other competitors if they have a problem with Rapunzel but none of them seems to have one. She tries to get Rapunzel to give up, but fails. She now wants to win the challenge of the brave.
Meanwhile, Eugene tries to get back into the arena but he left his ticket and money there, thus requiring to buy a new one. Because he has no money with him, he makes Rapunzel wigs and sells them to the people. With the final event drawing near, everyone chooses their weapons. Cassandra takes her sword while Rapunzel chooses a frying pan. All the weapons they have chosen are put into a wagon, but Rapunzel's frying pan falls out. Cassandra, still conflicted about Rapunzel's obliviousness, decides not to tell the assistant that her weapon fell out of the wagon. Eugene meanwhile has earned enough money to buy a new ticket, but as it turns out they are all sold out. That means he now has to buy the one from Shorty but it appears harder than he thought.
The final challenge is about to begin. Feeling a bit guilty, Cassandra tries to tell Rapunzel about the frying pan falling out of the wagon but the competition starts before she can tell her. The competition involves the competitors battling one another and last one who remains inside the white ring wins. Cassandra picks up her bow, Wreck his club but Rapunzel cannot find her frying pan. Cassandra fights someone using a stick and is in the middle of defeating them before Wreck smashes her opponent out of the ring. Wreck and Cassandra defeat their opponents easily while Rapunzel decides to use her dancing fighting style again. Finally a battle between Cassandra and Wreck Marauder begins. The crowd is excited, but again they cheer for Rapunzel as she outwits the other competitors with her technique. Now only Wreck, Rapunzel and Cassandra are left. The crowd cheers for Rapunzel, making Wreck and Cassandra jealous. Cassandra pins Wreck to a post so she can defeat Rapunzel herself. She engages her friend in a fight with staffs. Wreck frees himself and hides behind the post as both girls battle one another. Cassandra easily overwhelms Rapunzel with her power, pushing her nearer to the ring. Rapunzel tries to talk her down, only for Cassandra to finally admit her feelings. She accuses her for not understanding how important this contest meant to her and how she is constantly disrespected by everyone around her. Cassandra goes on telling her how she always pushes her into the shadows. Rapunzel replies by telling Cassandra that she respects her and looks up to her, that being the reason why she took part at all. She apologizes for not realizing how important the contest was for her friend, and drops her stick. Suddenly, Wreck takes the chance to attack her with his club only to be intervened by Cassandra. She kicks him in the face, sweeps his leg making him trip and then lifts him into the air, throwing him outside the circle. By doing so, she steps on the line as well which leaves Rapunzel the winner. Knowing that she did not really defeat Wreck herself, she gives the trophy to Cassandra.
Meanwhile, Eugene buys the ticket from Shorty and sprints back into the stadium, only to discover the tournament's already over. Eugene furiously yells at Shorty for his money back as the episode ends.
- Mandy Moore as Rapunzel
- Zachary Levi as Flynn Rider
- Eden Espinosa as Cassandra
- Danny Trejo as Wreck Marauder
- Jeff Ross as Hook Foot
- Paul F. Tompkins as Shorty
- Sean Hayes as Pete the Guard
- Hannes Schroll as competitors' scream (archived audio)
- During the first challenge, the Goofy holler is heard when the first competitor flies through the air after being hit by a giant hammer.
- Four of Lady Caine's thugs appear in this episode.
- The bee-bearded woman may come from Vardaros as her picture is placed in Captain Quaid's office in season 2.
- One of Cassandra's duties is to fix the same dress that Rapunzel wears on her coronation from Tangled: Before Ever After.
- Running Gags: Eugene blows the horn louder to cheer Rapunzel but ends up kick out the stadium.