Jane has her knight in training 'rescue the damsel' test. It is a difficult challenge that she must meet in order to carry on her apprenticeship as a knight. But the challenge becomes more complicated when Jane makes a pact with the King to protect her friend, Pepper. If Jane fails, she sacrifices her bid to become a knight and faces a future in…the kitchens!
Dragon is feeling sick, very sick, with…a pig disease--curly tail. It is curable, but the antidote is a difficult quest away. Jane volunteers to go for the sake of her dear friend, and Sir Theodore sends Gunther with her to build their skills as knights. Meanwhile, Dragon is proving to be a very difficult patient.
Jester is the King’s best hope for winning the inter-kingdom competition of song. However, Jane’s overenthusiastic coaching results in Jester losing his voice. Hope is rekindled when Jane overhears a talented voice but unfortunately she cannot find the singer. Eventually, it turns out that Dragon is the silver throated singer but the problem is that singing is simply not acceptable dragon behavior.
When the King and Queen are gone for the day on royal business, Jane is entrusted with “protecting the royal heirs”. Unfortunately, babysitting the bratty Prince and playful Princess wreaks havoc on Jane’s plan to study for one of Sir Theodore’s knighthood tests. Jane asks Dragon to keep an eye on the two children but he manages to misplace the Princess in a game of hide n’ seek.
With the three-hundredth anniversary of the castle approaching, Jane and Gunther are given an important chore to prepare for the Royal Jubilee. Whichever squire polishes more of the castle's myriad of shields will win the honor of carrying the banner in the Jubilee Parade. At the same time, Dragon wants Jane to come to his cave to help him decipher the carvings on his wall.
While out on patrol, Dragon's spontaneous loop de loop causes Jane to slip off and free-fall through the air. Dragon manages to save her in the nick of time but is shaken by the experience. He vows that no harm will come to her and becomes something of an overprotective parent. Jane rebels against his suffocating affection and unlocks one of the secrets of her runic sword.
It is a proud day for Jane. The squires and knights must make their annual pledge of allegiance to the King. The day gets more exciting when Jane and Jester find a map of the catacombs and set off on a mission to find what they hope is treasure. Instead they stumble upon a terrible secret. Can Jane swear allegiance to the King if she have doubts about the current King's legitimacy?
When Sir Theodore assigns Jane the menial task of cleaning his sword, Gunther gloats over getting the easier task of Sentry duty. Dragon accuses Theodore of playing favorites, but Jane defends her mentor... until she discovers a broken sword in Sir Theodore's quarters with mysterious runes on its hilt.