Pineapple Upside Down Cakes 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.

CLASSIC PINEAPPLE UPSIDE-DOWN CAKE

Steps:

• Preheat oven to 375°. In an ungreased 9-in. square baking pan, combine butter and brown sugar. Drain pineapple, reserving 1/3 cup juice. Arrange 9 pineapple slices in a single layer over sugar (refrigerate any remaining slices for another use). Sprinkle pecans over pineapple; set aside. , In a large bowl, beat egg yolks until thick and lemon-colored. Gradually add sugar, beating well. Blend in vanilla and reserved pineapple juice. Combine flour, baking powder and salt; add to batter, beating well. , In a small bowl with clean beaters, beat egg whites on high speed until stiff peaks form; fold into batter. Spoon into pan., Bake 30-35 minutes or until a toothpick inserted in center comes out clean. Let stand 10 minutes before inverting onto serving plate. Place a cherry in the center of each pineapple slice. If desired, serve with whipped topping.

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 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.

SKILLET PINEAPPLE UPSIDE-DOWN CAKE

Steps:

• Preheat oven to 375°. Melt butter in a 9- or 10-in. ovenproof skillet. Add brown sugar; mix well until sugar is melted. Drain pineapple, reserving 1/3 cup juice. Arrange about 8 pineapple slices in a single layer over sugar (refrigerate remaining slices for another use). Sprinkle pecans over pineapple; set aside. , In a large bowl, beat egg yolks until thick and lemon-colored. Gradually add sugar, beating well. Blend in vanilla and reserved pineapple juice. Combine the flour, baking powder and salt; gradually add to batter and mix well. , In a small bowl, beat egg whites on high speed until stiff peaks form; fold into batter. Spoon into skillet. , Bake until a toothpick inserted in the center comes out clean, 30-35 minutes (cover loosely with foil if cake browns too quickly). Let stand 10 minutes before inverting onto serving plate. Place cherries in center of pineapple slices.

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.

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.

MINI PINEAPPLE UPSIDE-DOWN CAKES

Steps:

• In a small bowl, combine brown sugar and butter until blended. Spoon into 24 greased muffin cups. Drain pineapple, reserving the juice; spoon pineapple into prepared cups. Place a cherry half cut side down in the center of each., In a large bowl, combine the cake mix, eggs, oil and reserved pineapple juice. Beat on low speed for 30 seconds. Beat on medium for 2 minutes. Spoon over pineapple, filling each cup three-fourths full., Bake at 350° for 18-22 minutes or until a toothpick inserted in the center comes out clean. Immediately invert onto wire racks to cool.

FRESH PINEAPPLE UPSIDE DOWN CAKE

Steps:

• Preheat oven to 400 degrees F (205 degrees C).
• Melt the butter. Brush a little bit of the butter on the inside of a 9-inch cake pan.
• Mix 5 tablespoons of the butter with the dark brown sugar and 1/4 cup of the pineapple juice. Place this mixture in the bottom of the cake pan. Arrange the pineapple rings on the brown sugar mixture in a decorative pattern (be creative). Set pan aside.
• Stir together the flour, salt, white sugar, and baking powder.
• Separate the eggs. Beat the whites until stiff but not dry.
• Beat two of the egg yolks until lemony yellow. Stir in the remaining 1/2 cup pineapple juice, vanilla, and remaining melted butter. Add this mixture to the flour mixture. Gently fold in the egg whites. Pour batter over the top of the brown sugar and pineapple rings.
• Bake in the preheated oven until cake springs back when lightly touched with a finger, about 30 minutes. Let cake cool in pan for 10 minutes then cover pan tightly with a serving dish and invert so that the pineapple side is up.

PINEAPPLE UPSIDE-DOWN CAKE

Steps:

• Heat oven to 350°F. In 9-inch square pan, melt butter in oven. Sprinkle brown sugar evenly over melted butter. Arrange pineapple slices over brown sugar. Place cherry in center of each pineapple slice.
• In medium bowl, beat remaining ingredients with electric mixer on low speed 30 seconds, scraping bowl constantly. Beat on high speed 3 minutes, scraping bowl occasionally. Pour batter over pineapple and cherries.
• Bake 50 to 55 minutes or until toothpick inserted in center comes out clean. Immediately place heatproof serving plate upside down over pan; turn plate and pan over. Leave pan over cake a few minutes so brown sugar mixture can drizzle over cake; remove pan. Serve warm. Store cake loosely covered.

PINEAPPLE UPSIDE-DOWN CAKES

Steps:

• Tear off 4 sheets of nonstick foil. Mound 1 1/2 tablespoons light brown sugar and 1 tablespoon unsalted butter on each sheet. Top each mound with a 1/2-inch-thick pineapple ring and put a maraschino cherry in the middle, then top each with an upside-down shortcake shell. Fold in the sides of the foil and seal to form a packet. Grill over medium-high heat, 12 minutes. To serve, flip the cakes pineapple-side up.

PINEAPPLE UPSIDE-DOWN CAKE

Steps:

• Place a rack in the middle of the oven and preheat to 350 degrees F. Cut out a circle of parchment or wax paper and place it in the bottom of a 9 x 2-inch round cake pan. Lightly butter the sides of the pan.
• To make the topping: Heat a small saucepan over medium-high heat. Add the butter and cook, stirring occasionally, until it's browned and has a nutty aroma, about 5 minutes. Remove from the heat and whisk in the brown sugar and rum. Pour the butter-sugar mixture into the cake pan. Using a rubber spatula, spread the mixture out so it to covers the bottom of the pan.
• Quarter the pineapple lengthwise, core, and slice it into about twenty 3/8-inch-thick slices. Arrange some of the pineapple slices in a slightly overlapping ring around the inside of the pan, leaving the center open. Place 3 of the slices in the center in a triangle pattern. Press the slices into the butter-sugar mixture.
• To make the cake: Using a sieve over a large bowl, sift together the flour, baking powder, cinnamon, nutmeg, and salt. Set aside.
• In a large bowl with a hand-held electric mixer, combine the butter and sugar and mix at a low speed until just incorporated. Raise the speed to high and mix until light and fluffy, about 10 minutes. (Occasionally turn the mixer off, and scrape the sides of the bowl down with a rubber spatula.)
• Add the eggs one at time, waiting for each one to be fully incorporated before adding the next.
• Reduce the speed of the mixer to low. Add the flour mixture in 3 additions alternating with the milk in 2 additions. Raise the speed to medium and mix briefly until a smooth batter is formed.
• Pour the batter onto the pineapple-lined pan. Place the pan on a baking sheet and bake the cake, rotating the pan once during cooking, until golden brown and a toothpick inserted in the center of the cakes comes out clean, about 45 to 55 minutes. Remove the cake from the oven and let cool for 5 minutes.
• Run a knife around the edge of the pan to release the cake. Carefully invert the cake onto a serving plate and remove the parchment paper. Let cool completely before serving.

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.

MAKEOVER PINEAPPLE UPSIDE-DOWN CAKE

Steps:

• Pour butter into a 9-in. square baking pan; sprinkle with brown sugar. Arrange pineapple slices in a single layer in pan; place cherry halves in center of pineapple slices; set aside., In a large bowl, beat the sugar, milk, oil, egg and extracts until well blended. Combine the flour, baking powder and salt; gradually beat into sugar mixture until blended. Pour into prepared pan., Bake at 350° for 35-40 minutes or until a toothpick comes out clean. Immediately invert onto a serving plate. Serve warm.

PINEAPPLE UPSIDE-DOWN DUMP CAKE

Steps:

• In a microwave, melt 1/2 cup butter; stir in brown sugar. Spread evenly onto bottom of a greased 5-qt. slow cooker. Sprinkle with cherries and pecans; top with pineapple. Sprinkle evenly with dry cake mix. Melt remaining butter; drizzle over top., Cook, covered, on high until fruit mixture is bubbly, about 2 hours. (To avoid scorching, rotate slow-cooker insert a half turn midway through cooking, lifting carefully with oven mitts.), Turn off slow cooker; let stand, uncovered, 30 minutes before serving. If desired, serve with ice cream.

PINEAPPLE UPSIDE-DOWN CAKE

Steps:

• Heat oven to 180C/160C fan/gas 4.
• For the topping, beat 50g softened butter and 50g light soft brown sugar together until creamy. Spread over the base and a quarter of the way up the sides of a 20cm round cake tin. Arrange 7 pineapple rings on top (reserving the syrup for later), then place 7 glacé cherries in the centres of the rings.
• Place 100g softened butter, 100g golden caster sugar, 100g self-raising flour, 1 tsp baking powder, 1 tsp vanilla extract and 2 eggs in a bowl along with 2 tbsp of the reserved pineapple syrup. Using an electric whisk, beat to a soft consistency.
• Spoon into the tin on top of the pineapple and smooth it out so it's level. Bake for 35 mins. Leave to stand for 5 mins, then turn out onto a plate. Serve warm with a scoop of ice cream.

PINEAPPLE UPSIDE DOWN CAKE

Steps:

• Topping: Melt butter in a small skillet on direct heat.
• Add brown sugar and stir until well blended and bubbly.
• Pour into a 9" square baking dish, spreading to cover the bottom.
• (Alternately, microwave butter and brown sugar in a 9" square glass baking dish till well blended and bubbly).
• Arrange pineapple spears and maraschino cherry halves on top of the brown sugar in a sun-burst pattern.
• Chill in refrigerator while preparing batter.
• Batter: Sift together flour, salt and baking powder.
• Cream shortening/butter and sugar in a mixing bowl until light and fluffy.
• Add egg and vanilla and beat until smooth.
• At low speed, and in alternate additions, add in the flour and orange juice, beginning and ending with the flour mixture.
• Beat only until smooth.
• Remove cake pan from the refrigerator and spread batter over topping.
• Bake at 325 degrees for 40 minutes.
• Remove from oven, let stand for 5-10 minutes.
• Invert on a plate and serve warm.

PINEAPPLE UPSIDE-DOWN CAKE

Steps:

• Heat oven to 350 degrees. Line a baking sheet with parchment. Place cherries in a small heat-proof bowl. Bring 1 cup water to a boil in a small saucepan. Pour over dried cherries, and soak for 10 minutes. Drain well, and coarsely chop. Using a wide Japanese mandoline, slice whole pineapple as thinly as possible. Set aside. Sift together flour and baking powder. Set aside.
• Heat 1/2 cup of granulated sugar in a 10 1/2-inch cast-iron skillet. Cook until deep amber, about 5 minutes. Remove the pan from the heat. Add 4 tablespoons (1/2 stick) butter, stirring vigorously with a wooden spoon. Spread caramel evenly to coat the bottom of the skillet, and sprinkle with dark-brown sugar.
• Center one piece of pineapple in the skillet. Place pineapple slices in a tightly overlapping circle. Make a second ring, completely covering the bottom and continuing at least halfway up the sides. Place one remaining slice in the center of the skillet on top of the circles. (Be certain that there are no gaps as the bottom will be the top upon inversion).
• In a heavy-duty mixer fitted with the paddle attachment, cream remaining butter, remaining 3/4 cup of granulated sugar, and vanilla-bean scrapings. Add eggs one at a time, mixing well after each addition. Pour in milk and almond extract. Slowly add sifted flour, scraping sides as needed. Using a rubber spatula, fold in chopped cherries. Pour batter into pineapple-lined skillet. Spread batter evenly with an offset spatula.
• Place skillet on a prepared baking sheet, and transfer baking sheet to oven. Bake until golden brown and cake tester comes out clean, about 45 minutes.
• Meanwhile, pour cream into the bowl of a heavy-duty mixer. Add rum. Whip on high speed until stiff peaks form, 45 to 60 seconds. Remove cake from oven, and pour excess liquid from skillet into a measuring cup. Carefully invert onto large cake plate, and pour reserved liquid over cake. Serve with rum-spiked whipped cream.

LAYERED PINEAPPLE UPSIDE-DOWN CAKE

Steps:

• Preheat the oven to 325 degrees F (165 degrees C). Grease the bottom and sides of two 9-inch round, 1 1/2-inch tall cake pans.
• Combine brown sugar and butter for topping in a saucepan over medium heat; stir until sugar dissolves and mixture is bubbly, about 3 to 4 minutes.
• Pour mixture into one of the prepared cake pans. Arrange pineapple rings in a single layer on top.
• Whisk together both flours, baking powder, and salt for cake in a large mixing bowl. Beat sugar and butter in a separate bowl with an electric mixer until creamy and light. Add eggs, one at a time, beating well after each addition. Beat in vanilla. Add dry ingredients alternately with sour cream in two additions each, beating well after each addition.
• Pour 1/2 of the cake batter over the caramel and pineapple topping. Pour remaining cake batter into the second cake pan.
• Bake in the preheated oven until a toothpick inserted in the center of each cake comes out clean, 60 to 75 minutes.
• Remove from the oven and let sit in the pans for 5 minutes. Turn the cake without the topping layer onto a serving platter. Turn the cake with the topping layer on top of that. Serve warm.