Pineapple in Every Bite Upside-Down Cake Recipe

The thermometer may be (finally) rising, but with the snow and mud out there, you can’t quite embrace all the spring activities yet—so it’s the perfect time for a little baking. And with National Pineapple Upside Down Cake Day, which is observed annually on April 20, it’s also a good time to try your hand at this retro dessert.

Americans had been enjoying fruit upside down cakes since at least the late 1800s when many were made in cast iron skillets. However, the popularity of this dessert (unsurprisingly) soared after the folks with the Hawaiian Pineapple Company now known as Dole Pineapple perfected machinery to slice the fruit and later sponsored a baking contest in 1925 that produced a number of recipes for pineapple upside down cake. The cake then took off.

There are a lot of versions of this popular cake out there, many of which are made with rings of pineapple and those very sweet bright red maraschino cherries. By switching it up and using pineapple chunks, like in this cake version does, every slice of the cake will be completely topped with sticky, glazed pineapple, says pastry chef and cookbook author Elinor Klivans, who contributed this recipe to Real Food. No cake-only spaces between rings of pineapple here. Dark brown sugar produces the dark, sweet coating on the pineapple, and honey makes the glaze smooth.

Pineapple in Every Bite Upside-Down Cake

Makes 12 servings

14 cup (12 stick) unsalted butter
1 cup packed dark brown sugar
1 tablespoon honey
12 cup pineapple juice drained from pineapple chunks, for cake
234 cups pineapple chunks in juice, about 112 (20-ounce) cans

112 cups cake flour
1 teaspoon baking powder
14 teaspoon salt
12 cup (1 stick) soft unsalted butter
1 cup sugar
2 large eggs
1 teaspoon vanilla extract

1. Preheat the oven to 350°F. Line the bottom of a 9-inch diameter cake pan with 2-inch-high sides with parchment paper.

2. For the glaze, in a saucepan, cook the butter, brown sugar, and honey for about 2 minutes until the butter and brown sugar melt and the mixture is smooth, stirring often. Pour the mixture evenly into the prepared pan. Reserving 12 cup of the pineapple juice, drain the pineapple and measure the 234 cups of pineapple chunks. Save any extra juice or pineapple for another use. Place the pineapple chunks neatly on the glaze, covering the glaze with pineapple. Set aside.

3. To mix the cake, sift the flour, baking powder, and salt together onto a piece of wax paper or into a medium bowl and set aside. Put the butter and sugar in a large bowl and beat with a mixer on medium speed until lightened in color and fluffy, about 3 minutes. Add the eggs 1 at a time, beating for 1 minute after each addition. Stir in the vanilla. On low speed, mix in half of the flour to incorporate it. Mix in the 12 cup pineapple juice. Mix in the remaining flour to incorporate it. Scrape dollops of batter from the bowl over the pineapple, and then spread it evenly.

4. Bake for about 50 minutes, until the top feels firm when touched lightly, and a toothpick inserted into the center of the cake—but not the pineapple—comes out clean.

5. Cool the cake in the pan for 5 minutes. Use a small sharp knife to loosen the sides of the cake from the pan. Place a wire rack against the top of the cake and invert it onto the wire rack to cool. Discard the parchment paper. The cake can be cooled for 20 minutes and served warm, or it can be cooled thoroughly and served at room temperature. Store the covered cake at room temperature up to 2 days and serve at room temperature.

Nutrition info (per serving): Calories 357 (111 From Fat); Fat 13g (Sat. 8g); Chol 66mg; Sodium 108mg; Carb 60g; Fiber 1g; Protein 3g

In her role as Senior Editor on Greenspring’s Custom Publications team, Mary leads Real Food magazine, the nationally syndicated publication distributed through our retail partner grocery stores. She also leads editorial on the nationally syndicated Drinks magazine and writes a weekly blog post focusing on food and drinks for the She rarely meets a chicken she doesn’t like, and hopes that her son, who used to eat beets and Indian food as a preschooler, will one day again think of real food as more than something you need to eat before dessert and be inspired by his younger brother, who is now into trying new foods.