Eight years prior, Flynn Rider and his partner in crime, Lance Strongbow work together with criminal kingpin, the Baron to raid a royal carriage and manage to steal several valuables. However, they are quickly double crossed by The Baron when his right-hand man, Anthony the Weasel steals everything they acquired under the Baron's orders. Flynn and Lance are left to face the guards themselves, but manage to escape. In the present day, Eugene and Rapunzel are in town collecting donations to give to the orphanage, but unknown to Rapunzel, Eugene notices a mysterious figure in the crowd watching them. During a brief stop back to the castle, Eugene notices the cloaked figure again and realizes he is following them. Eugene and Rapunzel attempt to escape, but find the figure blocking every exit. Eugene urges Rapunzel to hide while he confronts the figure, only to discover much to his surprise that it's none other than his childhood best friend and former partner in crime, Lance Strongbow who is quickly knocked unconscious when Rapunzel attacks him from behind. Returning to the castle, Lance is properly introduced to Rapunzel and Cassandra and reacquaints himself with Eugene after years apart. Lance and Eugene reveal their close friendship, revealing themselves as best friends growing up together and considers themselves the only family each other has ever had.
However, Cassandra reveals her suspicions of Lance, believing he has not reformed. While Eugene and Rapunzel defend Lance, Eugene has already realized Lance is up to no good and confronts him regarding his intentions. Lance confesses he needs Eugene's help. Lance reveals that his former cellmate, Oldie stole a great amount of treasure and hidden it away in an underground cave in Corona, but since he will be spending the remaining part of his life in jail, gave Lance a map to directions where the treasure is hidden and have it for himself. Eugene refuses to help, informing Lance his days as a thief are behind him, but Lance begins to persuade to Eugene, claiming that getting the treasure is his chance to reform and start anew and assures it is a victim-less crime since the treasure does not belong to anyone. Reluctantly, Eugene agrees to help, but on the strict condition that nobody finds out. Meanwhile, Cassandra reveals more of her suspicions of Lance to Rapunzel and soon Rapunzel begins to question Lance's return and intentions.
In his bedroom, Eugene is making preparations, but quickly hides his belongings away when Rapunzel arrives. Nervously, Eugene manages to hide the truth from Rapunzel when she reveals Cassandra's suspicions of Lance. Rapunzel is relieved and assures she trusts Eugene, but admits her growing worries and doubts about Lance. Eugene assures Rapunzel and they share a kiss goodnight, but shortly after she leaves, Lance appears outside the window. Lance and Eugene leave to retrieve the treasure, but not before Eugene shows a great amount of guilt and remorse for lying to Rapunzel. Eugene and Lance arrive at the underground cave, but Eugene shockingly discovers it's actually a basement filled with treasure. Eugene is angry at Lance for lying to him, who admits he lied knowing Eugene would never come along otherwise. Lance further confesses the owner of the basement is revealed to be none other than the Baron, revealing his true motive for the heist was to seek revenge against the Baron for double-crossing him and Eugene all those years ago and wants to settle the score. Lance and Eugene prepare to leave, but find the Baron's henchmen have found their exit. Eugene and Lance sneak through the Baron's home and despite a few close calls, manage to escape and run off into the woods. Meanwhile back at the castle, Rapunzel goes to visit Lance, but finds both him and Eugene missing and goes with Cassandra to search for them.
In the forest, Lance is delighted of the amount of treasure they managed to steal, but Eugene is greatly angered as not only did Lance lie to him, but took advantage of him and his loyalty and decides to end their friendship. Lance is surprised as to how money has apparently truly changed him. Eugene assures he truly has changed into a better person, but corrects Lance that money had nothing to do with it, when infact Rapunzel helped to change him for the better. However, they are interrupted when Eugene hears Rapunzel's voice and upon noticing her and Cassandra nearby, hides away the stolen treasure. Rapunzel and Cassandra question Eugene and Lance about their actions and while Eugene attempts to hide the truth, Cassandra becomes even more suspicious when she discovers a ring from the stolen loot. Rapunzel confronts Eugene about the ring's origins, but Lance steps in and lies to Rapunzel and Cassandra. Lance claims the ring belonged to their former mother figure nanny from the orphanage and they hidden the ring away in an Oak tree and promised whoever found true love first would give the ring to their special someone. Lance gives the ring to Rapunzel who is touched and flattered, but Eugene continues to feel more guilty. Returning to the castle, Rapunzel notices the royal crest on the ring and believes the owner must have originated from Corona. However, upon closer inspection of the ring, Eugene finally remembers the identity of it's true owner, recalling it originally belonged to Rapunzel's mother and his future mother-in-law, Queen Arianna.
Back at the castle, Eugene is summarising the recent events and possibilities regarding the ring. Eugene realizes that once Queen Arianna sees Rapunzel wearing the ring, she will immediately learn he was responsible for the carriage robbery and if he tries to ask Rapunzel to return the ring, she will discover that he previously lied to her. Eugene ultimately realizes that no matter the outcome, the truth will be revealed and both Rapunzel and Queen Arianna will be devastated and disappointed with him. With no other options left, Eugene decides to steal back the ring, before they learn the truth. However, Lance refuses to help, but ultimately agrees when Eugene threatens to confess the truth and turn themselves in for their past and present crimes.
Eugene and Lance disguise themselves and sneak into Rapunzel's bedroom. They manage to retrieve the ring, but accidentally awaken both Pascal and Rapunzel in the process. They try to escape until they are stopped by Cassandra who quickly defeats Lance. Eugene attempts to sneak away until Rapunzel arrives and hits him with her frying pan and upon doing so learns the thieves to be Eugene and Lance. In Rapunzel's bedroom, Eugene and Lance have finally confessed the truth about everything, leaving Rapunzel furious. Eugene begins to apologize and takes full responsibility until Lance speaks up and finally owns up to his mistakes. Lance admits his wrong doings in taking advantage of both Eugene and their friendship and truly and genuinely apologizes for his actions and lies. Eugene decides the right thing now is to confess the truth to Queen Arianna. Rapunzel begins to reprimand Eugene, revealing his actions to be deceitful and he should confess, but refuses to let him do so. Rapunzel assures her love and forgiveness to Eugene, but is unsure if her parents will forgive him and begins to devise a plan to secretly return the ring. However, refusing to let Rapunzel get involved or in trouble because of his past actions, Eugene assures he is not going to handle the situation as Flynn Rider, but as Eugene Fitzherbert, meaning he handle the situation the right way and accept the consequences of his actions no matter what they maybe.
The next day in the throne room, Eugene has confessed the truth to Queen Arianna and returns her ring. Queen Arianna is appreciative about Eugene's honesty and apology, but admits despite the robbery being many years ago it was still quite traumatic and is unsure if she can forgive him. Eugene understands and is ready to face the full consequences of his actions, believing he maybe banished from Corona when the king learns the truth. Outside in the garden, Eugene presents Rapunzel with a new ring and once again apologizes, assuring hurting her is the last thing he'd ever want to do. Rapunzel and Eugene reconcile and share a heartwarming embrace as Queen Arianna watches them from afar. King Frederic approaches Arianna and notices the return of her lost ring. However, deciding not to reveal the truth or involve Frederic over the recent events, Arianna reveals Eugene "found it this morning", showing that Arianna has forgiven Eugene for his past actions. Back in the garden, Eugene is upset over Lance's departure, but is unsure if he is truly remorseful of his actions. However, Rapunzel reveals to Eugene that a man named Arnwaldo Schnitz made a large generous donation to the Corona orphanage. Eugene is happy of the news, realising Lance under his real name, donated all of the Baron's stolen treasure to the orphanage, showing he has truly reformed.
- Mandy Moore as Rapunzel
- Zachary Levi as Flynn Rider
- Eden Espinosa as Cassandra
- James Monroe Iglehart as Lance Strongbow
- Clancy Brown as King Frederic
- Julie Bowen as Queen Arianna
- Paul F. Tompkins as Shorty
- Sean Hayes as Pete
- Gideon Emery as Weasel
- Chris Sonnenburg as Percival
- Rapunzel's awkward sleeping position references the way Anna sleeps in Frozen.
- The pink flower ring that Eugene gives Rapunzel - after he had given Arianna back her stolen ring - is similar to the ring that Robin Hood had given to Maid Marian.
- Chris Sonnenburg, the executive producer of the series, voices the character Percival in this episode.
- This is the first episode to show Rapunzel in her nightgown.