Classic pineapple upside down cake with caramelized pineapple rings and cherries.

Pineapple Upside Down Cake Recipe

Classic pineapple upside down cake with caramelized brown sugar, juicy pineapple rings and cherries over a tender buttery cake.

Prep 20 min
Cook 40 min
Total 1 hr 30 min
Servings 8 servings
Difficulty Easy
Jump to Recipe Adapt This Recipe
Oven350°F · conventional Pan9 inches (in) round Air fryerConversion not recommended

Contains: Milk · Egg · Wheat

This recipe contains milk, egg and wheat. If you have additional food allergies, check the labels on packaged pineapple, maraschino cherries and vanilla extract before using them.

WHY IT WORKS

Why This Recipe Works

01

Caramelized Fruit Topping

Butter and brown sugar melt beneath the pineapple as the cake bakes, creating a glossy caramelized topping when the cake is inverted.

02

Keep the Cake Tender

Creamed butter and sugar, plus milk and pineapple juice, give the cake a soft buttery crumb without making the fruit layer soggy.

03

Flip While Warm

A short rest lets the cake set, while inverting it before the caramel cools completely helps the pineapple topping release cleanly.

WHAT YOU’LL NEED

Equipment

9-inch round cake pan, at least 2 inches deep
Two medium mixing bowls
Electric hand mixer or stand mixer
Wire cooling rack

THE RECIPE

Ingredients & Method

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Measurements
Servings

My Notes

Ingredients

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Measurements
  • Pineapple Topping
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  • Cake
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Method

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  1. Heat the oven to 350°F. Grease the sides of a 9-inch round cake pan that is at least 2 inches deep, then line the bottom with a round of parchment paper.
  2. Pour the 1/4 US cup melted butter into the prepared pan and spread it over the bottom. Sprinkle the brown sugar evenly over the butter. Arrange 1 pineapple ring in the center and the remaining 6 rings around it, then place a maraschino cherry in the center of each ring.
  3. In a medium bowl, whisk together the flour, baking powder and salt until evenly combined.
  4. In a second bowl, beat the 1/2 US cup softened butter and granulated sugar with an electric mixer on medium speed for about 2 to 3 minutes, until lighter and fluffy.
  5. Beat in the eggs one at a time, mixing well after each addition, then beat in the vanilla extract.
  6. Stir the pineapple juice and milk together. With the mixer on low speed, add the flour mixture in 3 additions, alternating with the pineapple juice mixture in 2 additions, beginning and ending with the flour. Mix only until no dry streaks remain.
  7. Spoon the batter carefully over the arranged fruit and spread it gently to the edges. Bake for 35 to 40 minutes, until the top is golden and a toothpick inserted into a cake-only area near the center comes out clean or with a few moist crumbs.
  8. Set the pan on a wire rack and cool for 10 minutes. Run a thin knife around the edge. Place a serving plate upside down over the pan, hold the plate and pan firmly together, then invert them in one confident motion. Lift away the pan and carefully peel off the parchment paper.
  9. Let the cake cool for at least 20 minutes before slicing. Serve warm or at room temperature.

COOKING GUIDANCE

Practical Cooking Notes

Make Ahead

Bake and invert the cake, let it cool completely, then cover and refrigerate it for up to 2 days. Bring it toward room temperature before serving for a softer crumb and more pronounced pineapple flavor.

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Dietary options

Make This Recipe Work for You

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Already Vegetarian ✓
Make It Dairy-Free

Change the following ingredients:

Replace1/4 US cup unsalted butter, melted

With1/4 US cup unsalted plant-based butter, melted

Use the same quantity of a plant-based butter suited to cooking or baking as required.

Replace1/2 US cup unsalted butter, softened

With1/2 US cup unsalted plant-based butter, softened

Use the same quantity of a plant-based butter suited to cooking or baking as required.

Replace1/4 US cup whole milk, at room temperature

With1/4 US cup unsweetened neutral plant milk, at room temperature

Use the same quantity of an unsweetened neutral plant milk; flavor, protein and browning can differ.

For allergies, intolerances or strict dietary requirements, check the labels of the specific products you use. These swaps do not certify a recipe or ingredient as allergen-free.

Recipe Notes

Ingredient Notes

Use pineapple rings packed in juice rather than syrup so the topping stays balanced and some of the juice can flavor the batter. Drain the rings and cherries well, then pat them dry before arranging them in the pan.

Useful Substitutions

Dark brown sugar can replace light brown sugar for a deeper caramel flavor. If using fresh pineapple, cut evenly sized rings and replace the reserved canned juice with the same amount of unsweetened pineapple juice.

INGREDIENT QUALITY

Quality Note

Drain the pineapple rings and maraschino cherries thoroughly and pat them dry. Excess liquid can dilute the brown-sugar topping and leave the surface of the cake wet rather than glossy and caramelized.

SPEND LESS

Cost-Saving Tip

Use pineapple rings packed in juice and reserve some of that same juice for the batter. One can supplies both the fruit topping and the pineapple flavor for the cake without requiring a separate bottle of juice.

COOKING TIPS

Tips

Dry the Fruit Well

Excess pineapple or cherry juice can thin the caramel layer and make the surface wet, so drain the fruit thoroughly and pat it dry before arranging it.

Keep the Cake Tender

Once the flour is added, mix only until the batter is smooth and no dry streaks remain. Overmixing can make the finished cake tougher.

Spread the Batter Gently

Spoon the batter over the arranged fruit, then spread it carefully to the edges so the pineapple rings and cherries stay in place.

Invert After 10 Minutes

Let the cake stand in the pan for 10 minutes, then invert it while the caramel is still warm enough to release from the pan.

MAKE IT LAST

Storing, Freezing & Reheating

Storing

Once completely cool, cover the cake and refrigerate it for up to 4 days. For the best texture, let individual slices sit at room temperature briefly before serving.

Freezing

Freeze fully cooled individual slices in an airtight container, separating layers with parchment paper. Use within about 2 months and thaw overnight in the refrigerator.

Warm in the Oven

Place slices on a parchment-lined baking sheet and warm at 300°F for about 8 to 10 minutes, just until the cake loses its refrigerator chill.

Warm in the Microwave

Microwave one slice for about 10 to 15 seconds at a time until lightly warmed. Avoid overheating, which can make the cake rubbery and the topping very hot.

ESTIMATED PER SERVING

Nutrition

1 of 8 servings

415 kcal Calories
19 g Fat 24% DV
12 g Saturated fat 60% DV
58 g Carbohydrate 21% DV
1 g Fiber 4% DV
40 g Sugars
32 g Added sugars 64% DV
4 g Protein
190 mg Sodium 8% DV
95 mg Cholesterol 32% DV

Nutrition information is an estimate. Where shown, % Daily Value uses standard US Daily Values for adults and children aged 4+; actual values vary with ingredient brands, exact quantities and portion size.

QUESTIONS

Pineapple Upside Down Cake FAQs

Can I use fresh pineapple instead of canned?

Yes. Use evenly cut fresh pineapple rings and pat them dry well. Because the batter uses reserved canned pineapple juice, replace it with the same amount of unsweetened pineapple juice.

Why did my pineapple topping stick to the pan?

Sticking is more likely if the cake cools too long in the pan or the fruit is very wet. Line the base with parchment, drain the fruit thoroughly and invert the cake after the 10-minute rest.

Can I use pineapple chunks instead of rings?

Yes. Arrange well-drained pineapple chunks in a single layer over the brown sugar. The flavor will be similar, but the finished cake will not have the classic ring pattern.

How do I know when the cake is done?

The top should be golden and spring back lightly when touched. A toothpick inserted into a cake-only area near the center should come out clean or with a few moist crumbs.

Can I make pineapple upside down cake ahead of time?

Yes. Bake and invert the cake, let it cool completely, then cover and refrigerate it for up to 2 days. Bring it toward room temperature before serving for a softer crumb.

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