King Edmund arrives in Corona to see his long-lost son, Eugene, and to give him the royal sash of their bloodline. Eugene wants nothing to do with him, but Rapunzel invites him to stay. Later, the sash is stolen and a ransom note is left behind. Edmund and Eugene decide to go and retrieve it. Their quest begins to feel more like an outing as King Edmund reveals that Eugene's given name is Horace, which he deeply expresses his chagrin.
Meanwhile, the Stabbington Brothers plot revenge on Eugene as they are both viewed as a joke by the other criminals. They manage to locate him through the royal guards and Rapunzel takes off to warn them. Eugene and Edmund manage to fight off the Stabbington brothers, but then Eugene discovers that Edmund took the sash himself so that they can bond. The Stabbingtons abduct King Edmund, and Eugene and Rapunzel rescue him from a log flume. The royal sash gets destroyed in the attempt, but King Edmund, with help from Xavier, creates a new one for Eugene, and they make up.
Elsewhere, Cassandra tries to use her newfound Moonstone powers when she begins to hear a female voice softy saying her name; that of the Enchanted Girl, who had showed her everything of her girlhood past and abandonment by the unloving Gothel, and her drive to attain the Moonstone Opal for herself.
- Mandy Moore as Rapunzel
- Zachary Levi as Eugene Fitzherbert
- Bruce Campbell as King Edmund
- Eden Espinosa as Cassandra
- Sean Hayes as Pete
- Diedrich Bader as Stan
- Ron Perlman as The Stabbington Brothers
- Jennifer Veal as Enchanted Girl
- Jake "The Snake" Roberts as Doyle the Dart Player
- The opening sequence is updated.
- The title is a reference to one of the Lord of the Rings books by the same name by J.R.R. Tolkien.
- King Edmund arrives in Corona in this episode.
- Eugene makes a reference to the time when Shorty transformed into a peacock off screen and laid an egg in "Freebird".
- Eugene's birth name is revealed to be Horace.
- Eugene makes a reference to his line, "The kingdom and I aren't exactly simpatico at the moment" from Tangled. It is also revealed to be a quote from one of the Flynn Rider books.
- Rapunzel makes a reference to when she called a yo-yo a "hey-hey" and how Eugene mentioned it was already invented in "Great Expotations".
- Eugene wears the new sash that King Edmund and Xavier have made for him when he marries Rapunzel in Tangled Ever After.