Classic Pineapple Upside-Down Cake with Caramelized Pineapple and Cherries

Quick Recipe Version (TL;DR)

• Yield: 10 servings (one 9-inch round cake)
• Prep Time: 25 minutes
• Cook Time: 40–45 minutes
• Total Time: 1 hour 20 minutes (including cooling)

Quick Ingredients

• 1/4 cup (55 g) unsalted butter, plus more for greasing
• 3/4 cup (150 g) packed light brown sugar
• 1 can (20 oz / 560 g) pineapple rings in juice, drained (juice reserved)
• 10–12 maraschino cherries, drained
• 1 1/2 cups (190 g) all-purpose flour
• 1 1/2 tsp baking powder + 1/2 tsp fine salt
• 1/2 cup (120 ml) whole milk + 1/4 cup (60 ml) pineapple juice
• 2 tsp pure vanilla extract
• 3/4 cup (170 g) unsalted butter, softened
• 1 cup (200 g) granulated sugar
• 2 large eggs, room temperature
• 1/4 cup (60 g) sour cream (or plain yogurt)
• Whipped cream, for serving (optional)

Do This

• 1. Preheat oven to 350°F (175°C). Grease a 9-inch round cake pan (at least 2 inches deep) and line the bottom with parchment.
• 2. Melt 1/4 cup butter with brown sugar; pour into pan. Arrange pineapple rings and cherries snugly on top.
• 3. Whisk flour, baking powder, and salt. In a cup, combine milk, pineapple juice, and vanilla.
• 4. Cream 3/4 cup butter and sugar until fluffy. Beat in eggs one at a time, then sour cream.
• 5. Mix in dry ingredients alternately with milk mixture, beginning and ending with dry. Spread gently over fruit.
• 6. Bake 40–45 minutes until golden and a toothpick in the center comes out clean.
• 7. Cool 10–15 minutes, then invert onto a plate while still warm. Slice and serve warm or at room temperature.

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Why You’ll Love This Recipe

• Classic retro dessert with a tender, buttery vanilla cake and a glossy, caramelized pineapple topping.
• Uses pantry-friendly ingredients and canned pineapple, so you can make it any time of year.
• Beautiful presentation straight from the pan—no frosting or decorating skills required.
• Perfect for potlucks, family dinners, and holidays; it slices cleanly and serves easily.

Grocery List

• Produce: 1 can pineapple rings in juice; maraschino cherries.
• Dairy: Unsalted butter; whole milk; sour cream (or plain yogurt); optional whipped cream or ice cream for serving.
• Pantry: All-purpose flour; light brown sugar; granulated sugar; baking powder; fine salt; pure vanilla extract; nonstick spray or extra butter/oil for greasing.

Full Ingredients

For the Caramelized Pineapple Topping

• 1/4 cup (55 g) unsalted butter
• 3/4 cup (150 g) packed light brown sugar
• 1 can (20 oz / 560 g) pineapple rings in juice, drained
  • Reserve 1/4 cup (60 ml) of the juice for the batter
  • Pat the rings dry with paper towels so they caramelize nicely
• 10–12 maraschino cherries, well drained and patted dry

For the Tender Vanilla Cake Batter

• 1 1/2 cups (190 g) all-purpose flour
• 1 1/2 tsp baking powder
• 1/2 tsp fine sea salt or table salt
• 1/2 cup (120 ml) whole milk, at room temperature
• 1/4 cup (60 ml) reserved pineapple juice
• 2 tsp pure vanilla extract
• 3/4 cup (170 g) unsalted butter, softened to room temperature
• 1 cup (200 g) granulated sugar
• 2 large eggs, at room temperature
• 1/4 cup (60 g) sour cream or full-fat plain yogurt, at room temperature

To Prepare the Pan

• Butter or nonstick spray, for greasing the pan
• 1 round of parchment paper, cut to fit the bottom of a 9-inch pan (optional but recommended)

To Serve (Optional)

• Lightly sweetened whipped cream or vanilla ice cream
• Extra maraschino cherries for garnish

Step-by-Step Instructions

Step 1: Prepare the pan and preheat the oven

Preheat your oven to 350°F (175°C) with a rack in the center position.

Grease a 9-inch round cake pan that is at least 2 inches deep (or a 9-inch cast-iron skillet) with butter or nonstick spray. For extra insurance against sticking, line the bottom with a round of parchment paper, then lightly grease the parchment as well. Set the prepared pan aside while you make the topping.

Step 2: Make the caramel-brown sugar pineapple base

In a small saucepan over medium heat, melt 1/4 cup (55 g) butter. Add the 3/4 cup (150 g) packed light brown sugar and cook, stirring constantly, until the mixture is smooth, bubbly, and looks like thick caramel, about 2–3 minutes. Do not let it burn.

Immediately pour the hot caramel into the prepared pan and tilt the pan gently so the caramel covers the bottom in an even layer.

Arrange the pineapple rings on top of the caramel. Place one ring in the center, then arrange the remaining rings in a circle around it, overlapping slightly if needed to fit. Nestle a maraschino cherry in the center of each pineapple ring. If you have extra cherries, tuck them into any gaps. Set the pan aside while you make the cake batter.

Step 3: Mix the dry and wet ingredients

In a medium bowl, whisk together the flour, baking powder, and salt until well combined and lump-free. This ensures the leavening is evenly dispersed in the batter. Set aside.

In a measuring cup or small bowl, stir together the whole milk, reserved pineapple juice, and vanilla extract. Bringing these ingredients to room temperature helps them blend smoothly with the butter mixture later and gives you a more tender cake.

Step 4: Cream the butter and sugar, then add eggs and sour cream

In a large mixing bowl (using a hand mixer or stand mixer with the paddle attachment), beat the 3/4 cup (170 g) softened butter with the 1 cup (200 g) granulated sugar on medium speed until very light, pale, and fluffy, about 3–4 minutes. Scrape down the sides and bottom of the bowl as needed. Proper creaming incorporates air, helping the cake rise and stay tender.

Add the eggs one at a time, beating well after each addition until fully incorporated. Mix in the sour cream until the mixture looks smooth and creamy. If the batter looks slightly curdled at this stage, it is fine; it will smooth out once the dry ingredients are added.

Step 5: Combine the batter and layer over the fruit

With the mixer on low speed, add the dry ingredients in three additions and the milk mixture in two additions, alternating: start with one-third of the dry ingredients, then half of the milk mixture, another third of the dry, the remaining milk mixture, and finish with the last third of the dry ingredients. Mix just until each addition is incorporated and the batter is smooth. Avoid over-mixing so the cake stays soft.

The finished batter will be thick but spreadable. Carefully spoon it over the arranged pineapple and cherries in the prepared pan. Use an offset spatula or the back of a spoon to gently spread the batter all the way to the edges, trying not to disturb the fruit layer underneath. Smooth the top as evenly as you can; the cake will level somewhat during baking.

Step 6: Bake until golden and fully set

Place the pan on the center rack of the preheated oven and bake for 40–45 minutes. The cake is done when:

• The top is a rich golden brown color.
• A toothpick or thin skewer inserted into the center (through the cake, not the pineapple) comes out clean or with just a few moist crumbs attached.
• The edges may pull slightly away from the sides of the pan.

If the top is browning too quickly before the center is done, loosely tent the cake with a piece of foil and continue baking until fully set.

Step 7: Cool, invert, and serve

Remove the cake from the oven and place it on a wire rack. Let it cool in the pan for 10–15 minutes. This brief cooling time allows the cake to set while the caramel topping is still fluid enough to release from the pan.

Run a thin knife or spatula around the edges of the cake to loosen it. Place a large, heatproof serving plate or cake stand upside down over the pan. Carefully and confidently invert the whole thing in one motion. Let it sit upside down for 30–60 seconds to encourage the caramel and fruit to drop, then gently lift off the pan. Peel away the parchment, if used.

If any pineapple or cherries remain stuck to the pan, simply lift them off with a spatula and place them back onto the cake like a little puzzle. Slice the cake into wedges and serve warm or at room temperature, with whipped cream or ice cream if you like.

Pro Tips

• Invert while warm: Do not let the cake cool completely before turning it out. Inverting at 10–15 minutes is the sweet spot; the caramel is still soft enough to release cleanly.
• Dry the fruit well: Pat the pineapple rings and cherries dry before arranging them. Excess moisture can thin the caramel and make the top too wet instead of glossy and sticky.
• Room-temperature ingredients: For the best texture, bring the butter, eggs, milk, and sour cream to room temperature so they blend smoothly and trap more air.
• Check pan depth: Make sure your 9-inch pan is at least 2 inches deep. Shallower pans may overflow; if in doubt, place the pan on a baking sheet to catch drips.
• Neat slices: Use a sharp, thin-bladed knife and wipe it between cuts. This helps keep the caramel and fruit looking tidy on each slice.

Variations

• All-fresh pineapple: Use fresh pineapple rings instead of canned. Slice into 1/2-inch thick rings and briefly pat dry. Replace the reserved pineapple juice in the batter with an equal amount of extra milk or bottled pineapple juice.
• Rum-kissed version: Stir 1–2 tablespoons of dark or spiced rum into the caramel sauce after removing it from the heat, and replace 2 tablespoons of the milk with rum for a subtle, grown-up flavor.
• Nuts for extra crunch: Sprinkle 1/3 cup chopped pecans or walnuts over the caramel layer before adding the pineapple rings for a toasty, nutty crunch.

Storage & Make-Ahead

Allow the cake to cool completely after inverting. Cover leftovers tightly with plastic wrap or store in an airtight container. The cake keeps well at room temperature for up to 2 days or in the refrigerator for up to 4 days. For the best flavor and texture, bring chilled cake back to room temperature or warm individual slices briefly in the microwave (10–15 seconds) before serving.

To make ahead, you can bake the cake up to 1 day in advance. Store it covered at room temperature. The caramel topping will soften slightly but still be delicious. This cake does not freeze quite as beautifully as some others because of the fruit topping, but if needed you can wrap individual slices well and freeze for up to 1 month. Thaw overnight in the refrigerator and bring to room temperature before serving.

Nutrition (per serving)

Approximate values for one of 10 servings (without whipped cream or ice cream): about 430 calories, 21 g fat (including about 13 g saturated fat), 58 g carbohydrates, 2 g fiber, 39 g sugar, 5 g protein, and 230 mg sodium. These numbers are estimates and will vary with specific brands and portion sizes.