This Pineapple Upside-Down Cake is a classic dessert that’s as delightful to make as it is to eat. Imagine a moist, buttery cake with golden caramelized pineapple rings and bright cherries on top—it’s sunshine in every bite! Whether you’re impressing guests or indulging your sweet tooth on a cozy evening, trust me, this recipe is an irresistible crowd-pleaser.
Why You’ll Love This Recipe
- Timeless Charm: A nostalgic dessert with a modern twist that’s easy to love and even easier to devour.
- Stunning Presentation: The caramelized pineapple and cherry topping is as eye-catching as it is delicious.
- Beginner-Friendly: Simple steps and pantry staples make this recipe approachable for any home baker.

Ingredients
Here’s what you’ll need to create this luscious dessert:
- Unsalted Butter: For a rich, buttery flavor and perfect caramelization.
- Brown Sugar: Creates that beautiful, sticky-sweet layer on top.
- Pineapple Rings: The star of the show—sweet, tangy, and caramelized to perfection.
- Maraschino Cherries: For a pop of color and classic retro charm.
- All-Purpose Flour: Forms the base of our moist and tender cake.
- Granulated Sugar: Sweetens the cake batter beautifully.
- Baking Powder: Ensures a light, fluffy texture.
- Salt: Enhances and balances the flavors.
- Pineapple Juice: Adds tropical sweetness and keeps the cake moist.
- Whole Milk: Contributes to the soft, tender crumb.
- Vanilla Extract: Elevates the flavor with its warm, aromatic notes.

Note: Exact measurements can be found below in the recipe card.
How to Make the Pineapple Upside-Down Cake
Step 1: Prep the Pan & Pineapple Topping
Preheat your oven to 350°F and grease a 9-inch round cake pan. Pour melted butter into the pan, sprinkle brown sugar evenly, and arrange the pineapple rings. Place a maraschino cherry in the center of each ring—it’s already looking gorgeous, isn’t it?
Step 2: Mix the Cake Batter
In a mixing bowl, whisk together the flour, granulated sugar, baking powder, and salt. Add the softened butter, eggs, pineapple juice, milk, and vanilla extract. Beat until smooth and creamy.
Step 3: Combine & Bake
Carefully pour the batter over the pineapple layer and spread it evenly. Bake for 40-45 minutes, or until the cake is golden and a toothpick inserted in the center comes out clean.
Step 4: Cool & Serve
Let the cake cool in the pan for about 10 minutes, then gently invert it onto a serving plate. Serve warm and let everyone marvel at your masterpiece!
Pro Tips for Making the Recipe
- Use Fresh Pineapple: For an extra burst of flavor, swap canned pineapple rings for fresh ones.
- Room Temperature Ingredients: Ensure the butter, eggs, and milk are at room temp for smoother mixing.
- Invert with Care: Place a plate over the pan, flip quickly but gently, and give the pan a slight tap to release the cake.
How to Serve
- Pair this cake with a dollop of freshly whipped cream or a scoop of vanilla ice cream for ultimate indulgence.
- Serve warm with a drizzle of caramel sauce for extra decadence.
Make Ahead and Storage
Storing Leftovers
Wrap the cake tightly in plastic wrap and keep it at room temperature for up to 2 days, or refrigerate for up to 5 days.
Freezing
Freeze individual slices in an airtight container for up to 3 months. Thaw in the refrigerator overnight before enjoying.
Reheating
Warm slices in the microwave for about 10 seconds to bring back that “just-baked” feel.
FAQs
1. Can I use a square cake pan instead of a round one? Yes! A square 8×8-inch pan works just as well. Adjust baking time slightly if needed.
2. How can I make this cake dairy-free? Substitute the butter with a plant-based alternative and the milk with almond or coconut milk.
3. Can I add spices to the batter? Absolutely! A touch of cinnamon or nutmeg adds a delightful warmth to the cake.
4. What if I don’t have maraschino cherries? You can skip them altogether or replace them with fresh cherries or berries for a unique twist.

Pineapple Upside-Down Cake
Equipment
- 9-inch cake pan
- Mixing bowls
Ingredients
Topping
- 1/4 cup unsalted butter melted
- 1/2 cup brown sugar packed
- 7 slices pineapple rings canned or fresh
- 7 maraschino cherries optional
Cake Batter
- 1 and 3/4 cups all-purpose flour
- 1 and 1/2 tsp baking powder
- 1/4 tsp salt
- 1/2 cup unsalted butter softened
- 3/4 cup granulated sugar
- 2 large eggs
- 1 tsp vanilla extract
- 1/2 cup pineapple juice from canned pineapple
- 1/4 cup milk
Instructions
- Preheat oven to 350°F (175°C). Grease a 9-inch cake pan.
- Pour melted butter into the cake pan and sprinkle with brown sugar.
- Arrange pineapple rings and cherries on top.
- In a bowl, whisk together flour, baking powder, and salt.
- Cream butter and sugar until fluffy. Add eggs and vanilla extract.
- Alternate adding dry ingredients and pineapple juice with milk. Mix until smooth.
- Pour batter over pineapple layer and bake for 45 minutes.
- Cool for 10 minutes, then invert onto a plate. Serve warm.