Bosses are special Monsters that appear in a special room at the end of every Floor. They have to be defeated in order to ascend in the floors and progress through the game.
| Boss | Encountered On |
|---|---|
| Frothy The Dragon | The Waking Floors, Classrooms |
| Some Harmless Markings | Classrooms, The Waking Floors |
| The Arrival Day Gifts | Classrooms |
| Cauldron of Yesterdayers | Cafeteria |
| Candelabra of Longing | Cafeteria |
| Sudsy the Inanimate | Cafeteria |
| Fortress Woundwort | |
| The Obsolete Operator | Classrooms, The Waking Floors (Chapter 2) |
| The Frozen Few | Cafeteria (Chapter 2) |
| Cyndar's Timekeeper | Dorm (Chapter 2) |
| The Disciplined | Dorm (Chapter 2) |
| The Friendly Footstools | Dorm (Chapter 2) |
| Regan | Terrace (Chapter 2) |
| A Leafy Oversight | Terrace (Chapter 3) |
| The Brick Pile | Terrace (Chapter 3) |
|
Dorm (Chapter 3) | |
| The Winged Overseer | Terrace (Chapter 3) |
| A Buoyant Double | Terrace (Chapter 4) |
| Dr. Bloodfather | Library |
| The Malady Ward | Library |
| The Imaginaries | Library |
| Better Cordy | Library |
| The Administrator | Highest Library |
| His Natural Defenses | Paper Vortex |