Classic Pineapple Upside Down Cake

Here is my favorite pineapple upside down cake recipe, with a tender, moist cake and sweet caramelized pineapple rings that create the perfect finish when you flip it over.

This pineapple upside down cake is always a hit at family gatherings. I love how easy it is to make, and there’s something so satisfying about turning that cake pan upside down to reveal the beautiful pineapple topping. Plus, who doesn’t love cake that looks this good?

SAVE NOW

What Kind of Pineapple Should I Use?

For this classic cake, canned pineapple rings work much better than fresh pineapple. Fresh pineapple contains enzymes that can break down the cake batter and make it soggy, while canned pineapple has been heat-treated to remove these enzymes. Look for pineapple rings packed in pineapple juice rather than heavy syrup – the juice gives you better flavor control and you’ll actually use that reserved juice in the cake batter itself. Most grocery stores carry the standard 20-ounce cans with about 7-8 rings, which is perfect for a 9-inch cake pan. Just make sure to drain them well before arranging them in your pan so you don’t end up with a watery cake.

SAVE NOW

Options for Substitutions

This classic cake is pretty forgiving when it comes to swaps, so here are some options if you’re missing ingredients:

• Pineapple rings: Fresh pineapple works great – just slice it into rings about ½ inch thick. You can also use pineapple chunks or even other fruits like peaches, apricots, or pears for a fun twist.
• Brown sugar: If you’re out of brown sugar, mix 1 cup white sugar with 1 tablespoon molasses. In a pinch, you can use all white sugar, but you’ll lose some of that rich caramel flavor.
• Evaporated milk: Regular whole milk works fine as a substitute. You can also use buttermilk for a slightly tangy flavor, or even heavy cream if that’s what you have on hand.
• Pineapple juice: If you don’t have enough pineapple juice from the can, you can make up the difference with regular milk or even orange juice for a citrusy note.
• Maraschino cherries: These are totally optional for decoration. Fresh cherries, dried cranberries, or even chopped nuts work well, or you can skip them entirely.
• All-purpose flour: Cake flour will give you a more tender crumb – use 2¼ cups if substituting. Don’t use self-rising flour since this recipe already has baking powder.

Watch Out for These Mistakes While Baking

The biggest mistake when making pineapple upside down cake is not properly draining your pineapple rings, which can create a watery mess that prevents the brown sugar from caramelizing correctly – pat those rings completely dry with paper towels before arranging them in the pan.

Another common error is overmixing the cake batter once you add the flour, which leads to a tough, dense cake instead of the light, fluffy texture you want – mix just until the ingredients are combined.

Make sure to let the cake cool for exactly 5 minutes before flipping it out of the pan; any longer and the caramel will stick to the bottom, but flip too soon and the cake might fall apart.

Finally, don’t skip greasing your pan well, even if it’s non-stick, because that caramelized sugar can be stubborn and you want your beautiful pineapple design to come out perfectly intact.

SAVE NOW

What to Serve With Pineapple Upside Down Cake?

This sweet and fruity cake is pretty perfect on its own, but a scoop of vanilla ice cream on the side makes it even better – the cold creaminess pairs beautifully with the warm, caramelized pineapple. You could also serve it with a dollop of freshly whipped cream or even some coconut whipped cream if you want to play up those tropical flavors. A hot cup of coffee or black tea is my go-to drink pairing since the slight bitterness balances out all that lovely sweetness from the brown sugar and pineapple. For special occasions, try serving it with a small glass of dessert wine or even a tropical cocktail to keep the island vibes going.

Storage Instructions

Keep Fresh: This cake actually gets better after a day or two! Store it covered at room temperature for up to 3 days, or in the fridge for up to a week. The pineapple keeps it nice and moist, so don’t worry about it drying out quickly.

Freeze: You can freeze whole slices or the entire cake for up to 3 months. Wrap individual pieces in plastic wrap and then foil, or cover the whole cake tightly. It thaws beautifully and tastes just as good as fresh.

Serve: Bring refrigerated cake to room temperature for about 30 minutes before serving for the best flavor. If you’re serving frozen slices, let them thaw for about an hour. A quick 10-second zap in the microwave can warm up a cold slice if you prefer it slightly warm.

Estimated Nutrition

Estimated nutrition for the whole recipe (without optional ingredients):

• Calories: 2850-3100
• Protein: 30-36 g
• Fat: 110-120 g
• Carbohydrates: 440-480 g

Ingredients

For the fruit topping:

• 4 tbsp salted butter
• 1 cup brown sugar
• 1 can (20 oz) pineapple slices in juice, drained (reserve juice)
• Maraschino cherries, for garnish

For the cake batter:

• 2 cups all-purpose flour
• 3 tsp baking powder
• 1/4 tsp salt
• 8 tbsp salted butter (softened, 1/2 cup or 1 stick)
• 3/4 cup granulated sugar
• 2 eggs
• 1/2 cup evaporated milk
• 1 tsp vanilla extract
• 1/2 cup reserved pineapple juice

Step 1: Prepare the Skillet and Layer Pineapple

• 4 tbsp salted butter
• 1 cup brown sugar
• 1 can (20 oz) pineapple slices in juice, drained (reserve juice)

Preheat your oven to 350°F.

Generously spray a 10-inch iron skillet with cooking spray.

Add 4 tablespoons of salted butter to the skillet and place it in the preheating oven just until the butter is melted.

Once melted, carefully remove the skillet from the oven.

Sprinkle the brown sugar evenly over the melted butter, then neatly arrange the drained pineapple slices on top.

Set the skillet aside while you prepare the cake batter.

I always make sure to slightly overlap the pineapple slices for a beautiful pattern once the cake is inverted.

Step 2: Mix the Dry Ingredients

• 2 cups all-purpose flour
• 3 tsp baking powder
• 1/4 tsp salt

In a medium bowl, whisk together the all-purpose flour, baking powder, and salt until well combined.

Set aside; you’ll add the wet mixture to this bowl in the next step.

Step 3: Prepare the Wet Batter

• 8 tbsp salted butter (softened, 1/2 cup or 1 stick)
• 3/4 cup granulated sugar
• 2 eggs
• 1/2 cup evaporated milk
• 1 tsp vanilla extract
• 1/2 cup reserved pineapple juice

In a separate large bowl, use a hand or stand mixer to cream together the softened salted butter and granulated sugar until fluffy and light in color.

Beat in the eggs one at a time, ensuring each is thoroughly combined.

Add the evaporated milk, vanilla extract, and 1/2 cup reserved pineapple juice and mix until smooth.

Step 4: Combine Wet and Dry Ingredients

• dry mixture from Step 2
• wet mixture from Step 3

Add the wet mixture from Step 3 to the dry mixture from Step 2.

Mix just until all the ingredients are fully incorporated and the batter is smooth.

Avoid overmixing, as this can make the cake dense.

I like to fold the batter gently with a spatula for a tender crumb.

Step 5: Assemble and Bake the Cake

• pineapple and sugar skillet from Step 1
• cake batter from Step 4

Carefully spread the cake batter from Step 4 evenly over the arranged pineapple and brown sugar mixture in the skillet from Step 1.

Smooth the surface.

Bake in the preheated 350°F oven on the middle rack for 35 to 45 minutes, or until a toothpick inserted into the center comes out clean.

If the top seems to be browning too quickly, you can tent it with foil.

Step 6: Cool, Invert, and Garnish

• maraschino cherries, for garnish

Once baked, remove the skillet from the oven and allow the cake to cool for 10 to 15 minutes.

Run a knife around the edges if needed, then place a plate or platter over the skillet and carefully invert the cake so the pineapple is on top.

Decorate the top with maraschino cherries.

For a beautiful presentation, I like to put a cherry in the center of each pineapple ring.

SAVE NOW

Classic Pineapple Upside Down Cake

Delicious Classic Pineapple Upside Down Cake recipe with step-by-step instructions.

5 from 1 vote

Print Recipe Pin Recipe

Prep Time 19 minutes mins

Cook Time 38 minutes mins

Total Time 57 minutes mins

Servings 4

Calories 2975 kcal

Ingredients

  

For the fruit topping:

• 4 tbsp salted butter
• 1 cup brown sugar
• 1 can (20 oz) pineapple slices in juice, drained (reserve juice)
• maraschino cherries, for garnish

For the cake batter:

• 2 cups all-purpose flour
• 3 tsp baking powder
• 1/4 tsp salt
• 8 tbsp salted butter (softened, 1/2 cup or 1 stick)
• 3/4 cup granulated sugar
• 2 eggs
• 1/2 cup evaporated milk
• 1 tsp vanilla extract
• 1/2 cup reserved pineapple juice

Instructions

 

• Preheat your oven to 350°F. Generously spray a 10-inch iron skillet with cooking spray. Add 4 tablespoons of salted butter to the skillet and place it in the preheating oven just until the butter is melted. Once melted, carefully remove the skillet from the oven. Sprinkle the brown sugar evenly over the melted butter, then neatly arrange the drained pineapple slices on top. Set the skillet aside while you prepare the cake batter. I always make sure to slightly overlap the pineapple slices for a beautiful pattern once the cake is inverted.
• In a medium bowl, whisk together the all-purpose flour, baking powder, and salt until well combined. Set aside; you’ll add the wet mixture to this bowl in the next step.
• In a separate large bowl, use a hand or stand mixer to cream together the softened salted butter and granulated sugar until fluffy and light in color. Beat in the eggs one at a time, ensuring each is thoroughly combined. Add the evaporated milk, vanilla extract, and 1/2 cup reserved pineapple juice and mix until smooth.
• Add the wet mixture from Step 3 to the dry mixture from Step 2. Mix just until all the ingredients are fully incorporated and the batter is smooth. Avoid overmixing, as this can make the cake dense. I like to fold the batter gently with a spatula for a tender crumb.
• Carefully spread the cake batter from Step 4 evenly over the arranged pineapple and brown sugar mixture in the skillet from Step 1. Smooth the surface. Bake in the preheated 350°F oven on the middle rack for 35 to 45 minutes, or until a toothpick inserted into the center comes out clean. If the top seems to be browning too quickly, you can tent it with foil.
• Once baked, remove the skillet from the oven and allow the cake to cool for 10 to 15 minutes. Run a knife around the edges if needed, then place a plate or platter over the skillet and carefully invert the cake so the pineapple is on top. Decorate the top with maraschino cherries. For a beautiful presentation, I like to put a cherry in the center of each pineapple ring.