Pineapple Upside Down Cake
This Golden, sticky-sweet, and wonderfully retro Pineapple Upside Down Cake is the perfect treat for any occasion!

This recipe brings back memories of my childhood Sunday lunches, where a warm pineapple upside down cake often made a grand entrance on the dessert table.
I still remember the aroma of caramelized pineapple filling the kitchen and the excitement of flipping the cake to reveal its glossy, fruit-studded top.
This cake isn’t just a dessert, it’s a slice of nostalgia, made even better with a moist, buttery base and caramel soaked edges.
Why you’ll love this
- Beautiful Presentation: The glistening pineapple rings with cherries look impressive without needing any fancy decorating skills.
- Retro Charm: This dessert is a classic favorite that brings vintage vibes and sweet memories to the table.
- Incredibly Moist: The juicy pineapple topping seeps into the cake, making every bite extra tender and flavorful.
- One-Pan Wonder: Everything bakes together in one pan — flip it once, and you’re ready to serve!

Prep Time: 15 minutes
Cook Time: 45 minutes
Total Time: 1 hour
Cuisines: American
Servings: 8 slices
Estimated Cost: $6 – $8
Equipment:
- 9-inch round cake pan or cast-iron skillet
- Mixing bowls
- Whisk
- Spatula
- Hand or stand mixer (optional)
- Cooling rack
Ingredients

For the topping:
- ¼ cup unsalted butter (melted)
- ½ cup packed light brown sugar
- 6–7 pineapple rings (canned or fresh)
- Maraschino cherries (about 6–7, optional but classic)
For the cake batter:
- ½ cup unsalted butter (softened)
- ¾ cup granulated sugar
- 2 large eggs
- 1 tsp vanilla extract
- 1 ½ cups all-purpose flour
- 1 ½ tsp baking powder
- ¼ tsp salt
- ½ cup whole milk
- ¼ cup reserved pineapple juice (from the can)
Step-by-Step Instructions
Step 1: Prepare the topping
Pour the melted butter into your cake pan and swirl to coat the bottom. Sprinkle the brown sugar evenly over the butter. Arrange pineapple rings over the sugar layer. Place a maraschino cherry in the center of each ring. Set aside.
Step 2: Make the cake batter
In a bowl, cream the softened butter and sugar together until light and fluffy. Beat in the eggs one at a time, then stir in the vanilla. In another bowl, whisk together flour, baking powder, and salt.
Gradually add the dry ingredients to the wet mixture, alternating with the milk and pineapple juice. Mix until smooth and just combined.
Step 3: Assemble and bake
Pour the batter gently over the pineapple layer in the pan, spreading evenly with a spatula. Bake in a preheated oven at 350°F (175°C) for 40–45 minutes, or until a toothpick inserted in the center comes out clean.
Step 4: Flip and serve
Let the cake cool for 10 minutes in the pan. Run a knife around the edges to loosen. Carefully invert onto a serving plate. Let cool slightly before slicing.
Nutrition Facts (Per Slice)
- Calories: 320
- Fat: 14g
- Carbohydrates: 47g
- Sugar: 31g
- Protein: 3g
- Fiber: 1g
Note: Nutritional values may vary based on exact ingredients used.
Tips for Success
- Use room-temperature ingredients for a smoother batter and even baking.
- Don’t overmix the batter to keep the cake light and fluffy.
- Let it cool slightly before flipping to avoid breaking the cake but not too long that the topping sticks.
- Place a tray underneath your cake pan while baking to catch any syrup that might bubble over.
Common Questions
Can I use fresh pineapple instead of canned?
Yes! Just be sure to cut it into rings and remove the core. Canned pineapple is more traditional, but fresh adds a delicious touch.
Can I make this cake in advance?
Yes, you can bake it a day ahead. Store it covered at room temperature. Reheat slightly before serving for that warm, caramelized taste.
How do I store leftovers?
Wrap tightly in plastic or store in an airtight container. It will last up to 3 days at room temperature or 5 days in the refrigerator.
Can I freeze Pineapple Upside Down Cake?
You can! Wrap slices individually and freeze up to 2 months. Thaw and warm before serving.
Pineapple Upside Down Cake
Ingredients
For the topping
- ¼ cup unsalted butter melted
- ½ cup packed light brown sugar
- 6 –7 pineapple rings canned or fresh
- Maraschino cherries about 6–7, optional but classic
For the cake batter
- ½ cup unsalted butter softened
- ¾ cup granulated sugar
- 2 large eggs
- 1 tsp vanilla extract
- 1 ½ cups all-purpose flour
- 1 ½ tsp baking powder
- ¼ tsp salt
- ½ cup whole milk
- ¼ cup reserved pineapple juice from the can
Instructions
- Pour the melted butter into your cake pan and swirl to coat the bottom. Sprinkle the brown sugar evenly over the butter. Arrange pineapple rings over the sugar layer. Place a maraschino cherry in the center of each ring. Set aside.
- In a bowl, cream the softened butter and sugar together until light and fluffy. Beat in the eggs one at a time, then stir in the vanilla. In another bowl, whisk together flour, baking powder, and salt.
- Gradually add the dry ingredients to the wet mixture, alternating with the milk and pineapple juice. Mix until smooth and just combined.
- Pour the batter gently over the pineapple layer in the pan, spreading evenly with a spatula. Bake in a preheated oven at 350°F (175°C) for 40–45 minutes, or until a toothpick inserted in the center comes out clean.
- Let the cake cool for 10 minutes in the pan. Run a knife around the edges to loosen. Carefully invert onto a serving plate. Let cool slightly before slicing.
Notes
- Use room-temperature ingredients for a smoother batter and even baking.
- Don’t overmix the batter to keep the cake light and fluffy.
- Let it cool slightly before flipping to avoid breaking the cake but not too long that the topping sticks.
- Place a tray underneath your cake pan while baking to catch any syrup that might bubble over.
Thank you for stopping by and baking along!
I hope this Pineapple Upside Down Cake brings as much joy to your table as it does to mine.
Happy baking and sweet wishes to you and your loved ones!