Classic Pineapple Upside-Down Cake

Nov 3, 2026 · By VanillaGoods

Baking Cakes cupcakes Vanilla: Extract Easy

A butter cake baked over caramelized brown sugar, pineapple rings and cherries, then flipped so the glossy fruit sits on top. This is the familiar American skillet version. Makes 8 slices in about 1 hr 10 min.

Prep 25 min

Cook 45 min

Total 1 hr 10 min

Yield 8 slices

Ingredients

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slices

¼ cup (60 g)unsalted butter, for the topping
⅔ cup (150 g)light brown sugar
1 ¾ cups (450 g)canned pineapple rings, drained, about 8 rings, juice saved
1 ½ oz (40 g)maraschino cherries, 8 cherries, patted dry
1 ½ cups (190 g)all-purpose flour
2 tsp (8 g)baking powder
¼ tsp (2 g)salt
½ cup (115 g)unsalted butter, softened, for the batter
¾ cup (150 g)granulated sugar
2 (100 g)eggs, room temperature
1 tsp (5 ml)vanilla extract
¼ cup (60 ml)pineapple juice (from the can)
¼ cup (60 ml)whole milk

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Instructions

Heat the oven to 350 F (175 C). Melt the topping butter in a 10-inch (25 cm) oven-safe skillet, stir in the brown sugar until just bubbling, and remove from the heat.
Arrange the pineapple rings in the sugar, with a cherry in each center.
Whisk the flour, baking powder and salt together. Beat the butter and sugar 3 minutes until fluffy, then beat in the eggs one at a time and the vanilla.
Mix the pineapple juice and milk. Add the flour mixture to the batter in three parts, alternating with the liquid, and stir just until smooth.
Spread the batter gently over the fruit. Bake 40 to 45 minutes, until a skewer in the center comes out clean and the top is golden.
Cool 5 minutes only, loosen the edge with a knife, set a plate over the skillet and flip it in one quick move. Lift off the skillet and rearrange any fruit that shifted.
Serve warm or at room temperature.

Tips

Do not wait longer than 10 minutes to flip or the caramel sticks.
Pat the fruit dry to keep the caramel glossy.
Use a pan with sides at least 2 inches (5 cm) tall.
Good with vanilla ice cream.

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Recipe FAQ

How long does it take to make classic pineapple upside-down cake?

Plan on 25 minutes of prep and 45 minutes of cooking. The recipe makes 8 slices.

How should I store classic pineapple upside-down cake?

Cover and keep at room temperature up to 2 days or refrigerate up to 5 days. Rewarm slices briefly.

Can I make classic pineapple upside-down cake ahead?

It is at its best the day it is made; prepare it a few hours before serving.

Can I use a different form of vanilla?

Yes. This recipe uses 1 tsp vanilla extract (5 ml). Each teaspoon of pure vanilla extract can be swapped for 1 teaspoon of vanilla bean paste, the seeds of half a vanilla bean, or 1/2 teaspoon of vanilla powder. Paste and seeds add the classic dark specks.

Estimated · per serving

Nutrition

Per serving = 1 of 8 servings this recipe makes.

453 Calories / serving

19.5g Fat

66.8g Carbs

4.6g Protein

45.8g Sugar

Whole recipe (8 servings): ~3624 cal · 156g fat · 534g carbs · 37g protein · 366g sugar

Estimated values per serving, calculated from standard ingredient data. Not verified Nutrition Facts; actual values vary with brands, measurements, and preparation.