Marge gets food poisoning following a meeting with Miss Peyton about Bart entering middle school soon. This leads to Marge having feverish nightmares about her children growing up too fast and leaving her as an empty nester while she simultaneously has to help with preparations for the school's Bounce-A-Thon event.

Homer becomes suspicious of a new neighbor that wants to be his friend and happens to own a sports car dealership, fearing that he's being buttered up into buying an expensive new car. But when Homer lets his guard down, he discovers there was another motive related directly to the property next door itself. Meanwhile after Nelson ramps up his bullying to a new level, Lisa uses technology to counter him only for Nelson to enlist Hubert Wong's help to fight back.

Guest stars: Rosalie Chiang as Hubert Wong and Dick Van Dyke as himself

A mockumentary about the rise and fall of the company LifeBoat, the brainchild of a young college dropout CEO named Persephone Odair who charmed Mr. Burns into funding her questionable new venture that she claims can flawlessly desalinate ocean water into drinkable water at a fraction of the cost.

The three stories for this Treehouse of Horror installment are:

• "Wild Barts Can’t Be Token": Bart is digitized into an NFT and Marge enters the digital realm to rescue him. Though she manages to rescue Bart, Homer digitizes himself to live the good life as a valuable NFT until the market crashes leaving him worthless and trapped.
• "Ei8ht": In an alternate outcome of the episode "Cape Feare", Sideshow Bob has killed Bart and Lisa grows up to become an expert in true crime. Lisa is brought in to help the police when a series of murders of her first-born childhood friends occurs. She enlists Sideshow Bob's help, but is later revealed to have a split-personality that committed the murders to allow her to get close to Bob and kill him in revenge for what happened to Bart.
• "Lout Break": Eating a radioactive doughnut causes Homer's burps to infect everyone with his DNA, turning them into versions of him. The children are immune, but fail to convince Homer to help find a cure....even when it infects Marge and the world.

Guest stars: Matthew Friend as Jimmy Fallon, Kelsey Grammer as Sideshow Bob, and Kylie Jenner as herself

When Marge is mocked by the neighborhood women because her kids have only ever given her home-made gifts, Bart and Lisa decide to try and get their mother a nice birthday present only to spend her birthday money on a spy kit instead. After hearing Marge confess to Ned Flanders that she feels her family thinks of her as an afterthought, a guilt-ridden Bart and Lisa seek to learn about their mother's past to make it up to her with various results. Meanwhile, Kirk Van Houten thanks Homer for saving him from an exposed live wire as Homer begins scouring Springfield for other dangers to warn everyone about, resulting in him fearmongering the whole town.

When Bart's attempt to avoid dancing with girls in gym class results in the school being wrecked, Principal Skinner doesn't believe that it was an accident instead of a prank and puts him in Groundskeeper Willie's shack for detention. But this only causes Bart and Willie to bond over a mutual feeling that women have caused them both misery. When Willie goes missing and seems to have been kidnapped back to Scotland, Bart drags the whole family with him to save his new friend. Meanwhile, Homer tries his best to convince Marge that destination weddings are a bad thing.

At Lisa's behest the Simpson family all board a pop culture-themed cruise ship which Taika Waititi is on. It is here where Comic Book Guy reveals his latest pride and joy: a rare Radioactive Man action figure accidentally manufactured with Wolverine claws. But when the valuable figure is beheaded mere moments after its unveiling, Bart becomes the primary suspect because of a recent altercation he had with Comic Book Guy, and Lisa finds herself playing detective to find out the truth.

Guest stars: Maurice LaMarche as Hedonismbot Cosplayer and Taika Waititi as himself

Homer and Bart bond when they both become pro-cheaters at blue-collar sporting events, making Marge suspicious when Homer keeps winning competitions for things he’s never done before. Meanwhile, Lisa tries to get into the University of Springfield’s Summer Camp program.