The Best Pineapple Upside Down Cake Recipes

PINEAPPLE UPSIDE DOWN CAKE

Steps:

• Preheat oven to 350°F (177°C).
• Pour 1/4 cup melted butter into an ungreased 9×2 inch pie dish or round cake pan. (Make sure the pan is 2 inches deep. I recommend this pie dish, which is 1.8 inches deep but I never have an overflow issue.) Sprinkle brown sugar evenly over butter. Blot any excess liquid off the fruit with a clean towel or paper towel. (The wetter the fruit, the more likely the cake could overflow or the topping could seep over the sides when inverted.) Arrange about 6-7 blotted pineapple slices and all the cherries on top of the brown sugar. I like to halve 3 pineapple rings and arrange them around the sides of the pan, too. See my photo and video above for a visual of the arranged topping. Place pan in the refrigerator for a few minutes as you prepare the cake batter. This helps solidify or "set" the topping's arrangement.
• Whisk the cake flour, baking powder, baking soda, and salt together. Set aside.
• Using a handheld or stand mixer fitted with a paddle or whisk attachment, beat the butter on high speed until smooth and creamy, about 1 minute. Add the sugar and beat on high speed until creamed together, about 1 minute. Scrape down the sides and up the bottom of the bowl with a rubber spatula as needed. On high speed, beat in the egg whites until combined, then beat in the sour cream and vanilla extract. Scrape down the sides and up the bottom of the bowl as needed. Pour the dry ingredients into the wet ingredients. Turn the mixer onto low speed and as the mixer runs, slowly pour in the pineapple juice and milk. Beat on low speed just until all of the ingredients are combined. Do not over-mix. You may need to whisk it all by hand to make sure there are no lumps at the bottom of the bowl. The batter will be slightly thick.
• Remove topping from the refrigerator. Pour and spread cake batter evenly over topping.
• Bake for 43-48 minutes, tenting foil on top of the cake halfway through bake time to prevent the top from over-browning before the center has a chance to fully cook. The cake is done when a toothpick inserted into the center of the cake comes out mostly clean- a couple moist crumbs are OK. Don't be alarmed if your cake takes longer or if the cake rises up and sticks to the foil. (We serve the cake upside down anyway!)
• Remove cake from the oven and cool on a wire rack for just 20 minutes. Invert the slightly cooled cake onto a cake stand or serving plate. Some of the juices from the topping will seep over the sides- that's ok. You can slice and serve the cake warm, but the slices will be messy. I find it's best to cool the cake completely at room temperature before slicing and serving. Do not refrigerate the cake to speed up the cooling process because it could end up tasting overly dense.
• Cover leftover slices and store for up to 3 days in the refrigerator or 3 months in the freezer. Thaw at room temperature. I don't recommend freezing the cake as a whole because the topping arrangement doesn't thaw very nicely. See make ahead instructions below.

PINEAPPLE UPSIDE-DOWN CAKE FROM SCRATCH

Steps:

• Preheat the oven to 350 degrees F (175 degrees C). Grease a 9-inch diameter, 2 1/2-inch tall round cake pan.
• Stir brown sugar and melted butter together in a bowl. Spread evenly over the bottom of the prepared cake pan. Place pieces of pineapple on top of brown sugar mixture and around the outer edge of the pan, all facing the same way. Place 2 pieces in the center. Place a cranberry between each pineapple piece.
• Beat white sugar and softened butter together using an electric mixer in a bowl until light and fluffy. Add eggs, one at a time, beating well and scraping the sides of the bowl after each addition. Pour in baking powder, vanilla extract, almond extract, cinnamon, and salt. Mix well.
• Add 1/2 cup flour and 1/4 cup milk to batter at a time, mixing well after each batch until thoroughly blended.
• Pour batter over pineapple slices, making sure batter gets between them. Spread and smooth batter using an offset spatula.
• Bake in the preheated oven until a toothpick inserted into the center comes out clean, 40 to 45 minutes.
• Remove cake from the oven and let cool on a wire rack for 15 to 20 minutes. Run a knife around the edges of the cake to loosen. Place a plate over the cake pan and quickly invert, waiting a few seconds for it to fall if it doesn't immediately separate from the pan.

OLD FASHIONED PINEAPPLE UPSIDE-DOWN CAKE

Steps:

• Preheat oven to 325 degrees F (165 degrees C).
• In a 10-inch heavy skillet with a heat-resistant handle (I use a cast iron skillet), melt 1/2 cup butter over very low heat. Remove from heat, and sprinkle brown sugar evenly over pan. Arrange pineapple slices to cover bottom of skillet. Distribute cherries around pineapple; set aside.
• Sift together flour, baking powder, and salt.
• Separate the eggs into two bowls. In a large bowl, beat egg whites just until soft peaks form. Add granulated sugar gradually, beating well after each addition. Beat until medium-stiff peaks form. In a small bowl, beat egg yolks at high speed until very thick and yellow. With a wire whisk or rubber scraper, using an over-and-under motion, gently fold egg yolks and flour mixture into whites until blended. Fold in 1 tablespoon melted butter or margarine and almond extract. Spread batter evenly over pineapple in skillet.
• Bake until surface springs back when gently pressed with fingertip and a toothpick inserted in the center comes out clean, about 30 to 35 minutes. Loosen the edges of the cake with table knife. Cool the cake for 5 minutes before inverting onto serving plate.

THE BEST PINEAPPLE UPSIDE DOWN CAKE

Steps:

• Preheat your oven to 350 degrees F. Lightly grease the bottom and sides of a 9" round cake pan with cooking spray. In a small bowl, combine the melted butter and brown sugar and pour the mixture into the bottom of the cake pan, spreading it out evenly. Arrange the pineapple rings around the pan and place maraschino cherries in between. Set aside briefly.
• In the bowl of a stand mixer, cream together the oil and granulated sugar until moistened. Beat in the egg, salt, baking powder, and vanilla until combined. Beat in the sour cream. Gradually add some of the milk, alternating with the flour until a soft batter comes together. Gently beat in the pineapple juice last.
• Carefully pour the batter over the pineapples in the pan, careful not to disturb their placement. Bake for approx. 40-45 minutes or until the cake appears set, is light golden brown, and a toothpick inserted near the center comes out clean or with moist, not wet, crumbs. Cool for 10-15 minutes, then very carefully invert the cake onto a platter or plate. Serve warm or room temperature.

PINEAPPLE UPSIDE-DOWN CAKE

Steps:

• Preheat the oven to 350 degrees F.
• Put the chopped pineapple in a baking dish, cover with foil and roast in the oven until soft and lightly golden brown. Leave the oven at 350 degrees F.
• Put the sugar, vanilla bean and 1/2 cup of water in a medium saucepan and cook over high heat until it turns a light caramel. Add the chopped pineapple, cream, salt and arbol and cook until slightly reduced. Let cool for about 5 minutes before adding it to a blender. Remove the vanilla bean, then carefully transfer the mixture to a blender and blend until smooth. Strain through a medium mesh strainer into a bowl. Return the mixture to the saucepan and reduce it to a sauce consistency. Pour the caramel into a seasoned 10-inch cast iron pan and let cool slightly. Arrange the pineapple slices on top of the caramel and set aside.
• Cream the butter and sugar in the bowl of a stand mixer fitted with paddle attachment until light and fluffy, scraping down the sides and bottom of the bowl once. Add the eggs, 1 at a time, beating until each is incorporated.
• Whisk together the flour, cornmeal, baking soda, baking powder and salt in a bowl until combined. Whisk together the buttermilk, sour cream, rum, vanilla extract and vanilla seeds in a measuring cup. Alternate the dry and wet ingredients starting and ending with the flour and mix until just combined, scraping the sides and bottom of the bowl. Pour the batter over the pineapple in the cast iron pan and bake until the top is lightly golden brown and a toothpick inserted into the center comes out with a few moist crumbs attached, 30 to 40 minutes. Cool on a baking rack for 10 minutes, then invert onto a large platter. Let cool for 30 minutes before serving.

PINEAPPLE UPSIDE-DOWN CAKE

Steps:

• Preheat the oven to 350 degrees F. Make the cake batter: Combine the flour, baking powder, salt, granulated sugar, 1/2 stick butter, the shortening, milk, eggs, vanilla and 2 tablespoons pineapple juice in a large bowl. Beat with a mixer on medium speed until well combined. (There will still be a few small lumps in the batter.) Set aside.
• Melt the remaining 1/2 stick butter in a 12-inch cast-iron skillet over medium heat; swirl to thoroughly coat the skillet. Sprinkle the brown sugar over the butter, making sure it's evenly distributed-you want the entire surface of the butter to be covered in brown sugar. Do not stir. As soon as the sugar dissolves, remove from the heat and layer the pineapple slices over the top. If desired, place maraschino cherries in the centers of the pineapple slices.
• Pour the batter evenly over the pineapple slices and gently spread to even out the top. Bake the cake 30 to 40 minutes, or until a toothpick inserted into the center comes out clean.
• Immediately run a knife around the edge of the cake, then put a plate upside down on top of the skillet. Carefully invert the skillet so the cake is turned onto the plate. It should come out pretty easily; if bits of cake stick to the skillet, use a small knife to patch it together. Let cool slightly before cutting into wedges. It's best served warm.

PINEAPPLE UPSIDE-DOWN CAKE

Steps:

• Preheat oven to 350 degrees. In the bowl of a mixer fitted with the whisk attachment, beat together flour, granulated sugar, baking powder, and salt. Add oil and milk; beat on medium speed until smooth, about 1 minute. Beat in egg and vanilla until well combined.
• Melt butter in a 10-inch nonstick skillet, preferably cast iron, over medium heat. Add brown sugar and cook, stirring, until moistened. Remove from heat; arrange pineapple and pecans on top. Pour batter evenly over top and smooth with a spatula.
• Bake until a tester inserted in center comes out clean, 45 to 50 minutes. Let cool in pan 10 minutes. Run a knife around edge of cake, then carefully invert onto a platter. Serve warm or at room temperature, garnished with cherries if desired.

EASY PINEAPPLE UPSIDE-DOWN CAKE

Steps:

• Heat oven to 350°F (325°F for dark or nonstick pan). In 13x9-inch pan, melt butter in oven. Sprinkle brown sugar evenly over butter. Arrange pineapple slices on brown sugar. Place cherry in center of each pineapple slice, and arrange remaining cherries around slices; press gently into brown sugar.
• Add enough water to reserved pineapple juice to measure 1 cup. Make cake batter as directed on box, substituting pineapple juice mixture for the water. Pour batter over pineapple and cherries.
• Bake 42 to 48 minutes (44 to 53 minutes for dark or nonstick pan) or until toothpick inserted in center comes out clean. Immediately run knife around side of pan to loosen cake. Place heatproof serving plate upside down onto pan; turn plate and pan over. Leave pan over cake 5 minutes so brown sugar topping can drizzle over cake; remove pan. Cool 30 minutes. Serve warm or cool. Store covered in refrigerator.

PINEAPPLE UPSIDE DOWN CAKE

Steps:

• Preheat oven to 325 degrees Fahrenheit.
• Melt butter in a 9x13 pan in oven.
• Sprinkle brown sugar evenly over butter in pan.
• Drain canned pineapple into a measuring cup.
• Place pineapple slices evenly in pan, cutting the last two in half to cover pan.
• Place the maraschino cherry halves in the center of the pineapple slices, cut side up.
• Combine the rest of ingredients in a large mixing bowl on slow speed for 30 seconds.
• Beat on medium speed for 2 minutes.
• Pour batter into pan.
• Bake for 45 to 55 minutes, or until a toothpick comes out clean.
• Cool 5 minutes and turn cake out onto a serving platter, pineapple side up.