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The Kingdom of Enchancia is having its Royal Jubilee. When King Magnus arrives, Baileywick is greeted by his Castle Steward Slickwell, who gives him a double-headed snakepin. Baileywick gratefully accepts the gift and Slickwell wishes him luck before muttering to himself "You're going to need it." Baileywick suddenly gets a bad case of clumsiness and crashes into King Roland. Slickwell helps Roland up and introduces himself. In the castle, King Roland explains the Jubilee itinerary to everyone: The Kings and Queens will play some games and go on a cruise while the Princes and Princesses will be entertained by King Magnus' sorcerer Greylock the Grand and, to the shock of everyone, Cedric. Cedric and Greylock compete fiercely against each other to show who is more fun by conjuring up origamis then balloons then pinatas, and finally, a flying carousel that together they entertain the Princes and Princesses with for the rest of the day. All the Princesses, that is, except Sofia who skips the whole thing because she is very worried about Baileywick. After another clumsiness attack, Slickwell urges him to retire stating he must have become too old to continue being Castle Steward of Enchancia but Sofia defends him and tells him she'll help him out by becoming his junior steward and puts on an outfit similar to Baileywick's, with earrings and her hair curled up in a ponytail. Meanwhile, Slickwell reveals he's after Baileywick's job and that the pin he gave him is a cursed object.
The Kings and Queens are having sports in the castle courtyard and, thanks to Sofia, Baileywick is doing much better. Seeing the young Princess's aid as a threat, Slickwell deliberately interferes with Sofia's next attempt to help Baileywick on the pretext of cleaning her shoes and, without Sofia, Baileywick's clumsiness attacks cause another mishap. Slickwell again tries to convince Baileywick to retire stating, once again, that he's getting on in his years and that King Roland can surly find an able replacement but Sofia defends him and reminds Baileywick that when she first became a Princess she felt she couldn't do it and would have quit just like that if he and her parents hadn't supported her which encourages Baileywick to stay on. After the Jubilee cake is frosted, Sofia helps Baileywick bring it out perfectly. But this is made moot when Baileywick sneezes Roland into his Royal Gifts. This final humiliating mishap finally convinces Baileywick to resign as Castle Steward of Enchancia despite everyone's protests. Sofia tries to convince Baileywick not to retire by promising to do more that will make things easier for him like carrying things for him and serving the meals but Baileywick has made his decision. He appreciates everything Sofia has done for him and gives her the serpent pin Slickwell gave him before leaving to pack. Suddenly, Sofia and Clover both have clumsiness attacks that helps Sofia realize that Baileywick didn't get clumsy until Slickwell gave him the pin. Realizing the pin is what made Baileywick clumsy, they decide to confront Slickwell about it. But when they get to the kitchen, the pin causes Sofia to fall and knock Slickwell's bag off the table. Inside it, she finds a book called The Beginner's Guide To Magically Cursed Objects. Reading it, they find out that the pin is called the Pin of Klutzenheimer, a cursed pin that puts a clumsiness curse on anyone who even touches it. Because of these discoveries, Sofia and Clover both realize Slickwell gave the pin to Baileywick on purpose so he could steal the latter's job. Sofia tells Clover to make sure Slickwell doesn't get away with it and goes off to tell Baileywick of her findings.
When Clover finds Slickwell escorting everyone to the cruise, he decides to give Slickwell a taste of his own medicine by putting the pin on his rear causing him to have clumsiness attacks that end up endangering everyone onboard. Meanwhile, Sofia finds Baileywick just in time to tell him about the pin and Slickwell's plot against him. Together, they go off to confront Slickwell and arrive just in time to find the Royal Schooner in danger and, with help from Greylock and Cedric, they manage to rescue everyone onboard. Once everyone is safe, Roland apologizes to everyone about the cruise and mess. Slickwell offers to clean up the mess but Sofia steps forward and proceeds to tell everyone on the Royal Schooner about Slickwell's wrongdoings and the pin. Slickwell finally realizes that the reason why he started being clumsy is because the pin was somehow placed on him and finds it just in time to prove that Sofia is telling the truth, to everyone's fury. He tries to offer an explanation but Roland cuts him off and tells him his services are no longer required. Slickwell protests that Roland can't fire him because he works for King Magnus causing Magnus himself to step forward and instantly fire him. Slickwell tries to get him to change his mind but his plea is cut short by the pin's curse and the guards escort him to the gates and throw him out. Everyone gladly welcomes Baileywick back and the Jubilee celebration continues with him back in charge.
- Ariel Winter as Princess Sofia
- Darcy Rose Byrnes as Princess Amber
- Tim Gunn as Baileywick
- Tyler Merna as Prince James
- Wayne Brady as Clover
- Jess Harnell as Cedric the Sorcerer
- Mitchell Whitfield as Greylock the Grand
- Christian Borle as Slickwell
- Carlos Alazraqui as King Magnus
- Travis Willingham as King Roland II
- Sara Ramirez as Queen Miranda
- Sabrina Carpenter as Princess Vivian
- Michaela Zee as Princess Jun
- This is the second episode to feature Baileywick's name in the title. The first was "Baileywick's Day Off".
- This is also the second episode where he has a more active role as well.
- This is the third time Baileywick is negatively affected by magic. The first time was in the episode "Mom's the Word", when Marla the witch turned him into a frog, and the second was in "Mystic Meadows" when Cedric and Goodwin turned him and everyone else into snowmen. Although technically it wasn't a spell but the magic inside a cursed pin that made him clumsy.
- This is the fourth time Sofia becomes a supporting assistant for someone. The first time was when she became Cedric's apprentice in the episode "Cedric's Apprentice", Aunt Tilly's companion in Great Aunt-Venture, and when she acted as James's royal adviser in "King for a Day".
- Sofia gets a new hairstyle for the first time in this episode.
- Sofia wears earrings for the first time in this episode.
- This is the second time Sofia wears an outfit which replicates the one of another character. The first was the replica version of Aunt Tilly's from "Great Aunt-Venture".
- Greylock's name was first mentioned in the episode "Cedric's Apprentice", but the character was not shown then.
- This is the second episode who's song is a duet that Sofia and an antagonist both sing. The first was the episode "The Amulet of Avalor".
- This is the first time Miranda has called her husband Roland instead of Rollie since "Once Upon A Princess". Although, in the premiere she greeted him by his full name and Title, where as here she just said Roland.
- Moral: The best person to see to your needs is a loyal friend.
- When Sofia was singing to Baileywick, Slickwell was in a room next door to where she and Baileywick were, singing his plot out loud. But the door was wide open, and Sofia and Baileywick didn't even notice.
- In the first scene inside the castle Baileywick is seen without the pin.
- Sofia and Clover found Slickwell's bag in the kitchen, but Slickwell never carried anything with him when he arrived at the castle (except for the pin).
- When Sofia and Clover found out that the pin was making Baileywick clumsy, Sofia told Clover, "We need to talk to Slickwell". But Clover can't even talk to humans, except Sofia.