The fifth book is called The Austere Academy. Mr. Poe sends them to live at a Prep school. All the building look like tombstones. They have a mean vice principal named vice principal Nero. he made up weird punishments to things against the rules at the school. For example, If you are late or not there at vice principal Nero's violin recital (he is awful on the violin) you have to buy him a bag of candy and watch him eat it. And if you go into the main building you can't use your utensils for breakfast, lunch, or dinner. Olaf comes again. His disguise this time is as a gym teacher named coach Genghis . He invents this thing called S.O.R.E. which stands for special orphan running exercises. So Violet, Klaus, and Sunny have to run (or in Sunny's case crawl) from six o'clock pm till dawn the next morning. They meet friends, the Quagmire triplets one of them died in their house fire along with their parents. Violet and Klaus start failing class because of S.O.R.E. Sunny has to work as a secretary for vice principal Nero. They figure out Olaf's plan. Olaf them gets away with their friends, the Quagmire's. And he gets away again.

The sixth book is called the  Ersatz Elevator. Mr. Poe takes then to live with Jerome and Esmé Squalor. They live in a penthouse that is a block away from the Baudelaire's house which is now in ruins because it was burned. Olaf comes in another disguise, but this time he is an auctioneer named Gunther. Esmé is obsessed with things that are "in" so she is in charge of the auction. Jerome takes the kids to a restaurant and "Gunther" goes over to the penthouse to "talk about the auction" with Esmé. The elevator is not "in" so they have to climb up a lot of stairs to get to the top where the penthouse is. When no one was home the Baudelaire's opened the elevator doors ( with help from Violet). They go down the elevator by tying ties and extension cords together. When they get to the bottom they see the Quagmire triplets in a cage. When the Baudelaire's go back to get something to get them out, Olaf gets them out of the cage, and hides them in one of the auctioned off things. The Quagmires told them three letters V.F.D. Then Esmé traps them in the elevator shaft so they can not go to the auction. They get down and follow the hallway at the bottom of the elevator shaft. The hallway came out under their houses ashes. They then run to the auction. They have Mr. Poe try to buy the thing that starts with V.F.D. But they find out that this V.F.D. stands for very fancy dollies. Olaf then gets away with the triplets and Esmé who becomes his girlfriend.

The seventh book is called The Vile Village. They go under the care of a whole village, but the person that houses and feeds them is named Hector. He has to do chores everyday. In the morning, he cleans the south side of the village, and in the afternoon he cleans the north side. He does this because of the crows. When the Baudelaire's come they tell Hector about Olaf and what he has done. They also tell him about their friends the Quagmires. Hector said that he found a poem that looked like Isadora Quagmire's. They found out that this poem was actually one of Isadora's. They kept getting these poems. Then Olaf comes again this time disguised  as Detective Dupin. He hides the Quagmires in a fountain and the poems that they find are from Isadora. The poems help the Baudelaire's find the Quagmires. A man named Jacques Snicket comes and Olaf kills him and blames the murder on the orphans. Then Olaf gets away. The Baudelaire's are now known as the Baudelaire murderers.

The eighth book is called the Hostile Hospital. In this book they go to a hospital and try to find the filing cabinet with things that the Baudelaire's are trying to find. They then get trapped in the filing room with Esmé. Klaus and Sunny get out but Violet gets caught. Then Violet gets put asleep so they are going to operate on her. Klaus and Sunny dress up as a doctor and Olaf's assistants think they are the white faced lady's. Klaus has to "operate" on Violet but really they are to cut off her head. Klaus then tries to distract the people so her sleepiness wears off. then Olaf puts the hospital on fire and the orphans almost don't get out. To not get caught by the police the hide in the back of Olaf's car.