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Pineapple Upside Down Sheet Cake, sliced, on a cake platter.
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Easy Pineapple Upside Down Sheet Cake

This moist Pineapple Upside Down Sheet Cake has a light pineapple flavor and flavorful brown sugar glaze. Nobody would guess that it starts with a cake mix!
Prep Time20 minutes
Cook Time40 minutes
Course: Dessert
Cuisine: American
Servings: 20

Ingredients

  • 1 Box Yellow Cake Mix We used Duncan Hines Perfectly Moist (15.25 oz). I like to sift cake mix
  • 3.4 oz (Small box) Instant Vanilla Pudding (Do not prepare the pudding.)
  • ½ cup all purpose flour (60g)
  • ½ cup light brown sugar (100g)
  • 1 cup sour cream (242g)
  • 3 eggs room temperature (place in a bowl of warm water for 5 minutes if in a hurry)
  • 1 cup pineapple juice (reserved from the cans of pineapple rings that we are using on top of the cake.) (240g)
  • ½ cup Vegetable Oil (we use Canola oil) (108g)
  • teaspoons Vanilla extract (10g)

For the Brown Sugar Glaze and topping

  • cup (250g) packed light brown sugar
  • 6 tablespoons (84g) butter, melted (This is ½ stick plus 2 tablespoons) (We used unsalted butter).
  • 2 cans Pineapple Rings in their own juice (reserve the juice to use in the cake batter) We used two 20 oz cans with some leftover. This is for the top of the cake, use however many you like. For mine, I used 12 rings, plus slices of the rings here and there for filler.)
  • 1 small jar maraschino cherries We used 12 cherries.

Instructions

  • Generously grease (with vegetable shortening) and flour a 9x13 sheet cake pan. Preheat the oven to 350 degrees F.
  • Melt the butter (we melted ours in the microwave).
  • Pour the melted butter into the sheet cake pan, and sprinkle with the 1 ¼ cup of light brown sugar.
  • Remove 12 pineapple rings from the cans (or your desired amount). Set aside one cup of pineapple juice for the batter.
  • Arrange the pineapple rings on top of the brown sugar in the sheet cake pan in a single layer. You can fill in empty spaces between the pineapple rings with slices of pineapple if you'd like.
  • Remove 12 (or desired amount) of maraschino cherries from the jar and place in the center of each pineapple ring.

For the Cake Batter

  • Sift the cake mix into your mixing bowl. Add all of the other ingredients: instant vanilla pudding mix, eggs, brown sugar, flour, sour cream, pineapple juice, vegetable oil, and vanilla extract.
  • Mix at medium speed for one minute. Scrape the sides and bottom of the bowl and mix one more minute.
  • Pour or scoop the batter into the sheet cake pan, covering the brown sugar, pineapple rings, and cherries.
  • Bake for 40-45 minutes or until a skewer or until cake springs back when lightly touched and a toothpick inserted into the cake comes out clean or with just a few crumbs attached. Baking times may vary- check your cake for doneness as it approaches the 35 minute mark.
  • Cool the cake in the pan for 10 minutes before inverting it onto your cake platter or cake board. If your cake bakes up with a dome in the center, it is a good idea to minimize it- either by gently slicing away the dome with a serrated knife, or gently pressing it down using a clean dish towel.
  • Next, place the cake platter on top of the the cake pan, and carefully flip it all as one (using dish towels or oven mitts to protect your hands from the heat.)
  • Leave the sheet cake pan upside down for a minute or two to give the the glaze a little more time to drip down.
  • Serve warm or cool. If not serving right away, it is best to refrigerate and then remove from the refrigerator 2-3 of hours before serving. This cake tastes best when at least room temperature or warm. If served when cold, the texture will not be the same (because of the butter in the recipe.)

Notes

This recipe makes about 7 cups of cake batter. It baked to the top of the 9x13 pan (2 inch) that we used.
If your cake bakes up with a dome (as often happens with cake mix recipes), it is best to gently trim it away with a serrated knife. Some bakers prefer to minimize the dome by gently pushing it down for several seconds at a time using a clean dish towel.
If you do not remove or minimize the dome, the cake is more likely to develop a crack when it is flipped onto the cake platter.