Name: Classic Pineapple Upside Down Cake
Prep time: 20 min
Cook time: 45 min
Total time: 1 h 5 min
Cuisine: American
Ingredients: 7 pineapple rings; 7 maraschino cherries; 1/2 cup packed brown sugar; 1/4 cup unsalted butter (for topping); 1/2 cup unsalted butter (softened, for batter); 2/3 cup granulated sugar; 2 large eggs; 1 1/2 cups all-purpose flour; 2 teaspoons baking powder; 1/4 teaspoon salt; 1/2 cup milk; 1 teaspoon vanilla extract

I’ve always had a soft spot for nostalgic desserts, and the Classic Pineapple Upside Down Cake is right at the top of my list. There’s just something so satisfying about flipping that golden cake out of the pan and revealing the glossy pineapples and bright red cherries. It’s a retro showstopper that never fails to impress, whether I’m baking it for a family gathering or just because I need a slice of sunshine on a gloomy day.

What I love most is how deceptively simple it is to make. The ingredients are straightforward, but when they come together, they create a cake that’s moist, buttery, and beautifully caramelized. That luscious pineapple and cherry topping turns every bite into a warm, tropical escape. It’s a dessert that brings smiles — and second helpings — every time.

Why You’ll Love This Classic Pineapple Upside Down Cake

This cake isn’t just about looks — although those caramelized pineapples and cherries definitely catch the eye. It’s wonderfully rich without being heavy, and the tangy sweetness of the fruit balances the soft, buttery crumb underneath. Whether you’re new to baking or a seasoned pro, this is a cake you’ll find yourself making again and again. It’s a hit with all ages and always delivers a touch of vintage charm.

What Kind of Pineapple Should I Use?

Canned pineapple rings are ideal for this recipe because they’re uniform in size, perfectly tender, and easy to arrange in a circular pattern. Plus, they come packed in juice which adds extra flavor to the cake. Fresh pineapple can also be used, but it requires peeling, coring, and slicing — and even then, it may not have that same soft, syrupy texture after baking.

Options for Substitutions

If you’re looking to switch things up, you definitely have options. You can substitute the maraschino cherries with fresh cherries or even dried cranberries for a tart twist. For a more tropical flavor, swap part of the pineapple with sliced mango. Want a gluten-free version? Use your favorite 1:1 gluten-free baking flour blend. And if you’re dairy-free, replace the butter with a plant-based alternative and use a non-dairy milk like almond or oat.

Ingredients for this Classic Pineapple Upside Down Cake

Pineapple Rings – These form the iconic topping. Use canned rings for uniform shape and soft texture.
Maraschino Cherries – Nestled in the center of each pineapple ring, they add vibrant color and a burst of sweetness.
Brown Sugar – Essential for that rich, caramelized topping that forms as the cake bakes.
Unsalted Butter – Used in the topping and the cake batter, it gives the cake a rich, moist flavor.
Granulated Sugar – Adds sweetness to the cake base without overpowering the fruit.
Eggs – Provide structure and stability, ensuring a light, fluffy crumb.
All-Purpose Flour – The base of the cake; it gives the cake body and texture.
Baking Powder – Helps the cake rise and keeps the crumb tender.
Salt – Enhances the flavors and balances the sweetness.
Milk – Adds moisture and helps create a tender crumb.
Vanilla Extract – Adds a warm, aromatic note to complement the fruit.

Step 1: Prep the Pan and Topping

Grease a 9-inch round cake pan generously with butter or non-stick spray. Melt butter and brown sugar together, then pour this mixture into the base of the pan. Arrange pineapple rings in a single layer over the sugar, placing a cherry in the center of each ring.

Step 2: Mix the Dry Ingredients

In a medium bowl, whisk together the flour, baking powder, and salt. This ensures the leavening agents are evenly distributed for a uniform rise.

Step 3: Cream Butter and Sugar

In a large mixing bowl, beat the softened butter with granulated sugar until light and fluffy. This step incorporates air, giving your cake a delicate crumb.

Step 4: Add Eggs and Vanilla

Beat in the eggs one at a time, ensuring each is fully incorporated before adding the next. Then stir in the vanilla extract for added depth of flavor.

Step 5: Combine Wet and Dry Ingredients

Alternate adding the dry ingredients and milk to the butter mixture, starting and ending with the dry. Mix just until combined to avoid overmixing.

Step 6: Pour Batter Over Fruit

Carefully spread the cake batter over the arranged pineapples and cherries in the pan. Smooth the top with a spatula to ensure even baking.

Step 7: Bake

Place the cake in a preheated oven at 350°F (175°C). Bake for 40 to 45 minutes, or until a toothpick inserted into the center comes out clean.

Step 8: Cool and Invert

Allow the cake to cool in the pan for about 10 minutes. Then run a knife around the edges, place a serving plate over the pan, and flip it upside down in one quick motion. Let it rest a moment before lifting the pan off to reveal the glossy, golden top.

How Long to Prepare the Classic Pineapple Upside Down Cake

Preparation Time: The active prep time is about 20 minutes. This includes mixing the batter, preparing the topping, and arranging the fruit in the pan. If you’re using fresh pineapple, add another 5–10 minutes for slicing and prepping.

Baking Time: The cake bakes for 40 to 45 minutes at 350°F (175°C). Let it cool in the pan for at least 10 minutes before flipping. Factoring in all steps, you’re looking at just over an hour from start to serving.

Tips for Perfect Classic Pineapple Upside Down Cake

Make sure to pat the pineapple slices dry before placing them in the pan to avoid a soggy topping.
Don’t overmix the batter once you combine the wet and dry ingredients—mix just until combined.
Use room temperature butter and eggs for smoother blending.
Always invert the cake while it’s still warm; if you wait too long, the caramel topping can harden and stick to the pan.
Use a light-colored cake pan if possible—dark pans can overbrown the caramel and edges.

Watch Out for These Mistakes While Cooking

Using too much liquid: Avoid using pineapples packed in heavy syrup; juice-packed or fresh works best.
Overbaking: Check the cake a few minutes before the recommended time. Overbaking leads to a dry, crumbly texture.
Improper inversion: Be confident and quick when flipping the cake. Do it after cooling for just 10 minutes—not too soon, not too late.
Forgetting to grease the pan well: This cake relies on a clean release. Butter the pan generously or use a non-stick spray with flour.
Skipping the pat-down: If you don’t pat the cherries and pineapple slices dry, the topping can become watery instead of caramelized.

What to Serve With Classic Pineapple Upside Down Cake?

1. A scoop of vanilla ice cream

The creamy chill contrasts perfectly with the warm, caramelized cake.

2. Fresh whipped cream

Light and airy, it balances the rich buttery base.

3. Coconut flakes

Toasted coconut sprinkled on top adds a lovely tropical crunch.

4. Spiced rum sauce

Drizzle warm spiced rum sauce for an adult twist.

5. Fresh fruit salad

Bright and tangy fruits like kiwi, mango, and berries complement the cake beautifully.

Storage Instructions

Room Temperature: Store the cooled cake tightly covered at room temperature for up to 2 days. Use a cake dome or wrap it in plastic to keep the topping moist.

Refrigerator: For longer storage, refrigerate the cake for up to 5 days. Let it come to room temperature or gently warm it before serving to refresh the flavor and texture.

Freezer: You can freeze the cake (after it’s completely cooled) for up to 2 months. Wrap tightly in plastic wrap and foil. Thaw overnight in the fridge and warm before serving.

Estimated Nutrition

(Per slice – based on 10 servings)

Calories: 340 kcal
Total Fat: 14g
Saturated Fat: 8g
Cholesterol: 60mg
Sodium: 180mg
Carbohydrates: 52g
Sugars: 36g
Fiber: 1g
Protein: 3g

Frequently Asked Questions

How do I keep the pineapple from sinking?

Because the pineapple is laid down before the batter, it won’t sink. Just ensure your batter isn’t too thin.

Can I make this cake a day ahead?

Yes! In fact, it’s often better the next day after the flavors have melded. Just cover and store at room temperature or in the fridge.

Can I use fresh pineapple?

Definitely. Just peel, core, and slice into rings. Be sure to pat them dry thoroughly before placing in the pan.

What’s the best way to flip the cake?

Place a large plate over the warm cake pan, hold both firmly, and invert in one smooth motion. Let it sit a few seconds before removing the pan.

Can I make this in a different pan size?

Yes, an 8-inch square or even a 10-inch cast iron skillet works. Just adjust the bake time slightly depending on thickness.

Conclusion

The Classic Pineapple Upside Down Cake is a timeless dessert that proves simple ingredients can create showstopping results. With its sticky-sweet topping, tender cake crumb, and eye-catching presentation, it’s perfect for holidays, potlucks, or any day you need a little extra joy. Whether you’re a baking novice or a seasoned pro, this recipe will earn a place in your dessert rotation—just don’t be surprised when guests ask for seconds!