This cake is a timeless favorite that never goes out of style. The caramelized brown sugar and butter create a rich glaze that soaks into the pineapple, giving every bite deep, sweet flavor.
The contrast between the sticky fruit topping and the tender vanilla cake underneath is simply irresistible. It’s moist, flavorful, and perfectly balanced without being overly sweet.
It’s also surprisingly easy to make. With simple pantry ingredients and a straightforward method, you can create an impressive dessert that looks bakery-worthy but feels wonderfully homemade.
Ingredients
(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)
Preheat your oven to 350°F (175°C). Grease a 9-inch round cake pan.
Melt butter and pour it evenly into the bottom of the prepared pan.
Sprinkle brown sugar evenly over the melted butter.
Arrange pineapple rings over the sugar mixture and place a cherry in the center of each ring.
In a medium bowl, whisk together flour, baking powder, and salt.
In a separate large bowl, cream granulated sugar and softened butter until light and fluffy.
Beat in the eggs one at a time, then stir in vanilla extract.
Add the dry ingredients alternately with milk (or reserved pineapple juice), mixing until just combined.
Carefully spread the batter evenly over the arranged pineapple layer.
Bake for 40–45 minutes, or until a toothpick inserted into the center comes out clean.
Allow the cake to cool in the pan for about 10 minutes.
Run a knife around the edges, then carefully invert the cake onto a serving plate.
Servings and timing
Servings: 8–10 slices
Prep time: 20 minutes Bake time: 40–45 minutes Cooling time: 10–15 minutes Total time: Approximately 1 hour 15 minutes
Variations
For extra flavor, substitute some of the milk with reserved pineapple juice.
Add a splash of rum extract for a tropical twist.
You can use crushed pineapple instead of rings for a different texture.
Try adding a pinch of cinnamon to the brown sugar layer for subtle warmth.
Storage/Reheating
Store leftover cake covered at room temperature for up to 2 days or refrigerate for up to 5 days.
To freeze, wrap slices individually and store in a freezer-safe container for up to 2 months. Thaw overnight in the refrigerator.
To reheat, warm slices in the microwave for 10–15 seconds or in a 300°F (150°C) oven for about 5 minutes.
FAQs
Can I use fresh pineapple instead of canned?
Yes, fresh pineapple works well. Slice it evenly and consider lightly cooking it first to soften.
Why do I need to flip the cake while warm?
Flipping while slightly warm helps release the caramel topping cleanly from the pan.
Can I make this cake ahead of time?
Yes, it can be made a day in advance and stored covered.
What if my topping sticks to the pan?
Run a knife around the edges and gently tap the bottom of the pan before lifting it off.
Can I make this in a cast iron skillet?
Yes, a well-seasoned cast iron skillet works beautifully for even baking and caramelization.
How do I know when the cake is done?
Insert a toothpick into the center; it should come out clean or with a few crumbs.
Can I reduce the sugar?
You can slightly reduce the granulated sugar, but keep enough for proper texture.
Why is my cake dense?
Overmixing the batter can lead to a dense texture. Mix just until combined.
Can I make cupcakes instead?
Yes, layer the topping in muffin tins and reduce the baking time to about 18–22 minutes.
Does this cake need refrigeration?
It can sit at room temperature for short periods, but refrigeration is best for longer storage.
Conclusion
Homemade Pineapple Upside Down Cake is a nostalgic dessert that combines caramelized fruit with soft, buttery cake in every slice. Simple to prepare yet impressive to serve, this classic treat is perfect for family dinners, celebrations, or whenever you crave a taste of timeless comfort.
Homemade Pineapple Upside Down Cake is a classic dessert featuring caramelized pineapple rings and cherries baked beneath a soft, buttery vanilla cake. Once flipped, the glossy brown sugar pineapple topping creates a stunning presentation and delivers rich, nostalgic flavor in every bite.
Ingredients
For the Topping:
¼ cup unsalted butter, melted
½ cup brown sugar
6–8 canned pineapple rings (juice reserved)
6–8 maraschino cherries
For the Cake Batter:
1 ½ cups all-purpose flour
¾ cup granulated sugar
1 ½ teaspoons baking powder
¼ teaspoon salt
½ cup unsalted butter, softened
2 large eggs
½ cup milk (or reserved pineapple juice)
1 teaspoon vanilla extract
Instructions
Preheat oven to 350°F (175°C). Grease a 9-inch round cake pan.
Pour melted butter evenly into the bottom of the pan. Sprinkle brown sugar evenly over the butter.
Arrange pineapple rings over the brown sugar layer and place a cherry in the center of each ring.
In a medium bowl, whisk together flour, baking powder, and salt.
In a large bowl, cream softened butter and granulated sugar until light and fluffy.
Beat in eggs one at a time, then stir in vanilla extract.
Add dry ingredients alternately with milk (or pineapple juice), mixing just until combined.
Carefully spread batter evenly over the pineapple layer.
Bake for 40–45 minutes, or until a toothpick inserted in the center comes out clean.
Cool in the pan for 10–15 minutes.
Run a knife around the edges and carefully invert the cake onto a serving plate while still warm.
Notes
Flip the cake while warm to prevent sticking.Avoid overmixing to keep the cake tender.Add a splash of rum extract for a tropical twist.A cast iron skillet can be used for even caramelization.
