Pineapple upside-down cake is a delightful and visually stunning dessert that features caramelized pineapple slices and cherries atop a moist, buttery cake. The cake begins with a layer of brown sugar and melted butter, arranged with rings of pineapple and maraschino cherries in an eye-catching pattern. A rich, vanilla-infused cake batter is poured over the fruit, and the cake is baked until golden and fragrant. Once inverted, the cake reveals its beautiful, glossy fruit topping, with the caramelized sugar adding a sweet, sticky glaze. This nostalgic dessert combines the tropical flavors of pineapple with the comforting texture of a classic cake, making it a favorite for gatherings and celebrations.

Pineapple Upside Down Cake
Ingredients
TOP
- 1/4 cup salted butter melted
- 1/2 cup brown sugar
- 10 pineapple slices, patted dry
- maraschino cherries
CAKE
- 1/2 cup unsalted butter, softened to room temperature
- 3/4 cup granulated sugar
- 2 large eggs, at room temperature
- 1 tsp vanilla extract
- 1-1/2 cups all-purpose flour
- 1-1/2 tsp baking powder
- 1/4 tsp salt
- 1/2 cup whole milk, at room temperature
Instructions
- Preheat oven to 350F (175C).
- Pour melted butter into 9.5-10" pie plate or deep cake pan, make sure it entirely covers the bottom of the pan and use a spoon or spatula to grease the sides of the pan.
- Sprinkle brown sugar evenly over butter mixture. Arrange pineapple slices over the bottom of the pan, slice leftover slices in half and arrange up the sides of the pan.
- Place cherries in center of pineapple rings and as desired in empty spaces. Set aside.
- To prepare vanilla cake, beat butter and sugar in medium-sized bowl until creamy and well combined.
- Add eggs, beating one at a time until combined.
- Stir in vanilla extract.
- In a separate bowl, whisk together flour, baking powder, and salt.
- Alternate adding flour and milk to the wet ingredients, starting and ending with flour and mixing until just combined after each addition (I prefer to do this part by hand with a spatula to be sure not to overmix).
- Pour batter evenly over prepared cake pan over the pineapple/cherry layer.
- Bake at 350F (175C) for 30 minutes. At the 30-minute mark, loosely cover with foil and continue to bake (still on 350F/175C) for another 15 minutes, until a toothpick inserted in the center comes out mostly clean with few crumbs (total cook time for cake will be 45 minutes).
- Allow to cool for 10-15 minutes and then carefully invert the cake onto a serving platter (be careful, it will still be very hot!).
- Allow to cool before cutting and enjoying.