At Royal Prepatory Academy an art lesson begins with Flora and Merryweather telling the assembled princes and princesses that they'll be learning about enchanted paintings; paintings made with magic paintbrushes that allow the artists to jump into them and bring them to life. Pairings are made, with James and Amber being assigned to each other, to their disappointment, and Sofia being paired off with Hildegarde.
As Flora instructs them on the incantations and gestures required to enter and exit the enchanted paintings Hildegarde brags to Sofia about the enchanted paintings that can be found in her palace, making Sofia uneasy that she couldn't hear the full instructions. Meanwhile Amber and James are arguing about what to paint, with her wanting to paint a tea party set in an elegant location and his wanting to paint a safari scene.
Hilgegarde is now ready to enter the painting of a mermaid cove she painted with Sofia, but Sofia expresses concern that Hildegarde's gesturing incorrectly. Dismissing her concerns Hildegarde grabs Sofia's paintbrush and performs the incantation for entry, only for her gesturing to make the spell direct them to a painting made in a previous session that's hung up in the hallway outside. Hildegarde tries to cover her tracks by suggesting that she did this as a warm-up for Sofia and then attempts the exit spell, but gets the whole thing wrong. The character of the painting they're in offers to teach them the exit spell, having overheard it often enough from the classroom, in exchange for them retrieving a dog from another painting.
Meanwhile Amber's completed her painting and enters it with absolutely no difficulty, but James is adamant about getting a look-in with his safari ideas and decides to add some warthogs to the painting before following Amber in. The behaviour of the warthogs surprises James and alarms Amber, who's none too pleased about his meddling.
Sofia and Hildegarde can transition between paintings without any incantation, but they have to pass through them in sequence. Starting with a sepiatone flying derby scene, followed by an seafaring setting, Hildegarde constantly brags about her experience in these matters. However, after narrowly avoiding splashing down into sea and moving on to a scene reminiscent of Wei-Ling, Sofia starts hypothesizing that Hildegarde knows much less about these matters than she's letting on. Once they enter the next painting they find themselves facing an unusually large bull, Hildegarde dismissively remarking that it's hibernating, prompting Sofia to confront her about her ignorance in everything they've so-far faced. Their subsequent bickering arouses the bull, prompting them to make a quick getaway into the final painting, but Hildegarde loses her magic paintbrush in the process.
Amber and James are also in a dilemma as the warthogs are all but trashing the tea party setting, with James trying to placate them with food. Groaning over the absence of proper warthog food, James gives Amber the inspiration to resolve the issue by exiting the painting and setting brush to canvas again.
Sofia manages to coax the dog she and Hildegarde have been seeking and finds him only too happy to join the character in the first painting. Unfortunately the bull from the neighboring painting's managed to use Hildegarde's paintbrush to follow them in, causing momentary chaos as the princesses attempt to evade him. Having done so Sofia bemoans over having lost track of the dog, leading to Hildegarde proudly declaring that she can find him again, whereupon Sofia asks her outright what her plan is. As Hildegarde stumbles through her attempt to answer Sofia finally chews her out for getting them into this mess, despairing that they could well be locked into these artworks for their whole lives, and sets off to at least try and find the dog.
At this point the warthogs have James backed into a corner, making him wonder how they've been able to keep going after all this time. Just then a plate-load of vegetables appears on the table, distracting the warthogs, who are chided by Amber as she re-enters the painting. With firm instructions she successfully incorporates them into the setting.
Hildegarde's now hurrying after Sofia, after which she promptly admits that she never really knew anything about what they had to face and recalls how her first day at RPA led her to conclude that claiming to know everything was the only way she could gain respect from the other princesses. Sofia then tells her that being a smart alec was no way to gain respect, pointing out that knowing this gives Sofia some sense of respect for her. The sound of barking gets them back on track and they find the bull's cornered the dog. Hildegarde suddenly states that she's got a solution, and reassures Sofia that she means it. They successfully recover the dog, but the bull still goes after them. Hurrying back through the paintings they lose the bull after Sofia mentions how bulls pay more attention to sudden movements, allowing Hildegarde to distract it and recover her paintbrush. After getting back in the sea painting Hildegarde admits that she knows nothing about sailing, giving Sofia the opportunity to teach her on the way back. Finally reaching the first painting they allow the man to greet the dog before he tells them how to exit.
Back in class, Flora remarks upon the setting Sofia and Hildegarde had actually painted, allowing them to talk about their experiences in a roundabout way. Going past Amber and James Flora is stunned by their warthog tea-party.
Upon leaving the classroom, Hildegarde talks about how Sofia helped her find herself and gives her a hug, to Amber's consternation.
Tropes in this episode include:
- An Aesop: Never act like you know the answer when you actually don’t.
- A Day in the Limelight: Hildegarde has a bigger role in this episode.
- Beware the Nice Ones: Sofia may be a sweet girl, but she certainly has her limits, as shown when she's not only visibly annoyed by Hildegard's constant insistence that she knows everything but gives her the "Reason You Suck" Speech down below.
- Dark and Troubled Past: On Hildegarde’s first day at Royal Prep, she was resented by the other students and attempted to twirl like her older sister, only to trip up and everyone laughs at her. Since that day, she acted like she knew everything.
- Know-Nothing Know-It-All: Hildegarde's problem for the episode.
- "Not So Different" Remark: Sofia talks to Hildegarde that she too had a tough first day at school like she did, and had a similar experience where she tripped and everyone laughed at her as well.
- "The Reason You Suck" Speech: Sofia gives one to Hildegarde when she’s completely fed up with her constant know-it-all attitude.Sofia: Oh, stop it, Hildegarde! Just stop it! You act like you know everything, but you don't! And now, thanks to you, we're going to be stuck in these paintings forever!
