The group arrive in the town of Pincosta, but Eugene is immediately thrown in jail for having previously stolen the town's largest diamond, the Eye of Pincosta. The sheriff declares Eugene to work in the deadly copper mines for life and soon the rest of the group are thrown in jail. Rapunzel negotiates with the sheriff, offering to find and retrieve the Eye of Pincosta in exchange for her friends's release. The sheriff agrees, but on the condition that she returns within two days. Rapunzel confronts Eugene about the theft and reluctantly, reveals he previously worked together with Stalyan, forcing Rapunzel to seek her out and persuades her to help.
Rapunzel and Stalyan track down the owner of the jewel, Mr. Goodberry, who agrees to hand over the Eye if they participate in his wrestling match. Rapunzel agrees, but Stalyan double crosses her, revealing she stole back the Eye and intends to use it to free Eugene and win him back for herself.
Rapunzel is left to fight on her own and is soon outmatched, but Stalyan returns with a change of heart after finding a letter Rapunzel previously wrote to her, encouraging her there is good in everyone. Rapunzel and Stalyan fight together and are declared the winners and the two part ways, but not before Stalyan reveals her acceptance of Eugene and Rapunzel's love for each other. Rapunzel returns to Pincosta with the Eye, setting Eugene and her friends free.
- Mandy Moore as Rapunzel
- Zachary Levi as Flynn Rider
- Eden Espinosa as Cassandra
- James Monroe Iglehart as Lance Strongbow
- Jeff Ross as Hook Foot
- Paul F. Tompkins as Shorty
- Yvonne Strahovski as Stalyan
- Curtis Armstrong as Constable Lumph
- Lil Rel Howery as Virtuous St. Goodberry
- Danny Trejo as Malice Marauder
- Jake "The Snake" Roberts as Dart Playing Thug
- The tavern where Rapunzel and Stalyan met is named "Glass Sipper", referencing the Glass Slipper of Cinderella.