Pineapple Upside-Down Cake

Name: Pineapple Upside-Down Cake
Yield: 12 Servings
Ingredients: 1 cup (packed; 200 g) light brown sugar; 6 Tbsp. unsalted butter; 1 Tbsp. vanilla extract; 1 tsp. Diamond Crystal or ½ tsp. Morton kosher salt; 1 15-oz. can pineapple slices, drained, patted dry; 8 maraschino cherries (such as Luxardo), stems removed, patted dry; 2½ cups (288 g) cake flour; 1 Tbsp. baking powder; 1 Tbsp. Diamond Crystal or 1¾ tsp. Morton kosher salt; ¼ tsp. ground mace or freshly grated nutmeg; 3 large eggs, room temperature; 1 Tbsp. vanilla extract; 12 Tbsp. (1½ sticks) unsalted butter, room temperature; 1½ cups (300 g) granulated sugar; 1½ cups sour cream

By Cheryl Day

May 20, 2022

Photograph by Christopher Testani, Food styling by Victoria Granof, prop styling by Alex Brannian

Retro-favorite pineapple-upside down cake gets an easy upgrade courtesy of sophisticated Luxardo cherries in this recipe from cookbook author Cheryl Day. Deeply fruity and so-red-they’re-almost-black, Luxardos pack way more flavor than the saccharine, candy-colored maraschinos seen in many other iterations of this classic dessert. But don’t get too fancy: There’s no need to break down a whole pineapple here. While we do believe there is a time and place for fresh pineapple, this cake calls for canned pineapple rings, which are uniform in shape, always juicy, and never out of season. For the best flavor, look for rings packed in 100% pineapple juice.

If you’ve never flipped a cake before, you’re in for a treat. “The surprise when you unmold the cake,” writes Day in her cookbook Cheryl Day’s Treasury of Southern Baking, “is what makes [baking this style of dessert] so satisfying.” Expect a mosaic-like display of fruit arranged artfully, but effortlessly, on top of the cake, glazed with a caramelly topping of melted butter and brown sugar that keeps the dessert supremely moist and unabashedly delicious. A few things to keep in mind: Make sure your serving plate is wider than the cake pan; wait until the pan has cooled slightly; and invert with gusto, which helps ensure nothing will stick to the bottom of the pan.

Editor’s note: This recipe was originally published in October 2021.

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What you’ll need

Stand Mixer
$349 At Amazon
Luxardo Maraschino Cherries
$25 At Amazon
Metal Baking Pan
$28 $26 At Amazon
Scale
$27 At Amazon
Offset Spatula
$14 $13 At Amazon
Small Saucepan
$160 At Amazon
Microplane Grater
$17 At Amazon
Silicone Spatula
$13 At Amazon

Recipe information

Yield
12 Servings

Ingredients

Caramel Topping

1 cup (packed; 200 g) light brown sugar

6 Tbsp. unsalted butter

1 Tbsp. vanilla extract

1 tsp. Diamond Crystal or ½ tsp. Morton kosher salt

1 15-oz. can pineapple slices, drained, patted dry

8 maraschino cherries (such as Luxardo), stems removed, patted dry

Cake and Assembly

2½ cups (288 g) cake flour

1 Tbsp. baking powder

1 Tbsp. Diamond Crystal or 1¾ tsp. Morton kosher salt

¼ tsp. ground mace or freshly grated nutmeg

3 large eggs, room temperature

1 Tbsp. vanilla extract

12 Tbsp. (1½ sticks) unsalted butter, room temperature

1½ cups (300 g) granulated sugar

1½ cups sour cream

Preparation

Caramel Topping
Step 1
Place a rack in middle of oven and preheat to 350°. Place a 13x9" metal baking pan by the stove. Cook brown sugar, butter, vanilla extract, and salt in a small saucepan over medium heat, stirring occasionally, until butter is melted and mixture is bubbling, about 5 minutes. Pour caramel into baking pan and spread to evenly coat bottom with a heatproof rubber spatula, nudging into corners.
Step 2
Arrange pineapple slices on top of caramel without overlapping. Place a cherry in the center of each pineapple ring. Set aside.
Cake and Assembly
Step 3
Whisk flour, baking powder, salt, and mace in a medium bowl. Whisk eggs and vanilla extract in a small bowl.
Step 4
Beat butter and granulated sugar in the bowl of a stand mixer fitted with paddle attachment on medium-high speed until light and fluffy, about 4 minutes. Add egg mixture in 4 batches, beating on medium speed 30 seconds after each addition and scraping down bowl as needed. Reduce mixer speed to low and beat in dry ingredients in 3 additions, alternating with sour cream in 2 additions, mixing 30 seconds after each addition. Fold batter a few times with a clean spatula, scraping down sides to make sure everything is well mixed. Scrape batter into reserved baking pan; smooth surface.
Step 5
Bake cake until golden and a tester inserted into the center comes out clean, 40–50 minutes. Transfer pan to a wire rack; let cake cool in pan 15 minutes. Run an offset spatula along edges of cake to loosen. Set a large platter over pan and flip over to release cake; carefully remove pan. If any fruit or cake sticks to pan, scrape it off and press back onto top of cake. Serve warm or room temperature.
Do ahead: Cake can be baked 3 days ahead. Store airtight at room temperature.