Maw Maw’s Pineapple Upside Down Cake
There are some recipes that instantly transport you back to childhood, and this classic Pineapple Upside Down Cake is one of them. Sweet caramelized pineapples, bright red cherries, and a buttery golden cake come together in the most comforting way. It’s the kind of dessert you’d see cooling on Maw Maw’s kitchen counter, just waiting for someone to sneak a slice before dinner.
This recipe is simple, foolproof, and always a crowd-pleaser. Using a Bundt pan gives it that beautiful, old-fashioned presentation, and the shortcut cake mix keeps things quick without losing any of the homemade charm. The secret is the buttery brown sugar layer on the bottom, once you flip it, all that caramel goodness melts right into the fruit and cake.
Why You’ll Love This Recipe
- Classic Southern comfort – buttery, fruity, and perfectly caramelized.
- A vintage dessert that always impresses — beautiful when flipped from the Bundt pan.
- Quick and simple — uses pantry staples and a boxed cake mix.
- Perfect for gatherings — travels well and slices beautifully.
How to Make Maw Maw’s Pineapple Upside Down Cake
1
Prepare the pan
Preheat your oven to 350°F and spray your Bundt pan generously with Baker’s Pam. This ensures that perfect, clean release once it’s flipped.
2
Create the caramel layer
Whisk together the melted butter and dark brown sugar. Pour the mixture into the bottom of the Bundt pan, this is what gives you that beautiful golden glaze after flipping.
3
Add the pineapples and cherries
Arrange the pineapple slices over the brown sugar mixture and tuck a cherry into the center of each one. This step is what gives the cake its signature look.
4
Mix the cake batter
In a mixing bowl, combine the cake mix, eggs, and 1 cup of pineapple juice (add water if needed to reach one cup). Whisk until smooth.
5
Pour and bake
Pour the batter evenly into the pan and bake for about 25 minutes, or until a toothpick comes out clean.
6
Flip and reveal
Let the cake cool for 5 minutes. Then place a plate over the pan, flip confidently, and lift the Bundt pan away to reveal your caramelized pineapple masterpiece.
Maw Maw’s Pineapple Upside Down Cake
Ingredients
- 1 stick unsalted butter melted
- ½ cup dark brown sugar
- 1 box yellow cake mix
- 3 eggs
- 1 20 oz can pineapple slices, with juice
- Maraschino cherries
Instructions
- Preheat oven to 350°F. Grease a Bundt pan well with Baker’s Pam.
- In a small bowl, whisk the melted butter with the brown sugar. Pour this mixture evenly into the bottom of the pan.
- Arrange pineapple slices over the sugar mixture and place a maraschino cherry in the center of each slice.
- In a mixing bowl, combine the cake mix, eggs, and 1 cup of pineapple juice (add water as needed to make 1 full cup). Whisk until smooth.
- Pour the batter evenly over the pineapples and cherries.
- Bake for 25 minutes, or until a toothpick inserted in the center comes out clean.
- Let the cake cool for 5 minutes. Place a serving plate over the Bundt pan, flip carefully, and lift the pan away.
- Slice, serve, and enjoy!
