July 2, 2026
URL: https://www.bakingwithdolly.com/recipes/cakes-cupcakes/fresh-pineapple-upside-down-cake-10505
- Prep time 40 minutes
- Total time 120 minutes
- Servings 12
Ingredients
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1 small fresh pineapple
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1/2 cup butter
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1 cup firmly packed light brown sugar
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20 maraschino cherries
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1 pkg (15.25 oz each) Duncan Hines® Dolly Parton’s Yellow Cake Mix
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1 cup milk
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4 eggs
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1/2 cup melted butter
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fresh whipped cream
Nutrition Information
425 calories, 61g carbs
Directions
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Step one
Preheat oven to 350°F. Cut off top and bottom of pineapple. Cut and remove outer layer. If you have a pineapple corer, use it to remove the core. Otherwise, slice pineapple into 1/8th-inch thick slices and use a small cookie cutter to cut and remove core. Stack slices on top of each other and cut into quarters.
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Step two
Melt 1/2-cup butter in a 12-inch-deep cast iron skillet. Whisk in brown sugar; remove pan from heat. Shingle the pineapple slices and place them in an even layer over the bottom of the skillet. Spread maraschino cherries out evenly into the gaps between pineapple slices.
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Step three
In a large bowl, whisk together cake mix, milk, eggs, and 1/2-cup melted butter until well blended, about a minute. Pour cake batter over pineapple and spread evenly.
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Step four
Bake 45 to 50 minutes, until toothpick inserted in center comes out clean. Cool 15 minutes. Place a large serving platter on top of cake. Carefully invert your fresh pineapple upside down cake onto platter. Cool completely before slicing. Top each slice with whipped cream and enjoy!
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