Pineapple Upside-Down Cupcakes Recipe
Pineapple Upside-Down Cupcakes Recipe photo by Taste of Home
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Pineapple Upside-Down Cupcakes Recipe

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I have baked cupcakes for years since I served as a room mother for my three children. These easy-to-make, jumbo treats make an attractive dessert for special occasions or everyday. —Barbara Hahn, Park Hills, Missouri
TOTAL TIME: Prep: 30 min. Bake: 30 min. + cooling
MAKES:12 servings
TOTAL TIME: Prep: 30 min. Bake: 30 min. + cooling
MAKES: 12 servings


  • 6 tablespoons butter, cubed
  • 1 cup packed light brown sugar
  • 2 tablespoons light corn syrup
  • 1 small pineapple, peeled, cored and cut into 1/2-inch slices
  • 12 maraschino cherries, well drained
  • 3 eggs
  • 2 cups sugar
  • 1 cup canola oil
  • 1 cup (8 ounces) sour cream
  • 2 teaspoons vanilla extract
  • 2-1/2 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon salt
  • Whipped topping, optional

Nutritional Facts

1 each: 602 calories, 29g fat (9g saturated fat), 82mg cholesterol, 264mg sodium, 82g carbohydrate (61g sugars, 1g fiber), 5g protein.


  1. Line the bottom of 12 greased jumbo muffin cups with waxed paper; grease the paper and set aside.
  2. In a small saucepan, melt butter over low heat; stir in brown sugar and corn syrup. Cook and stir over medium heat until sugar is dissolved. Remove from the heat. Spoon 1 tablespoonful into each muffin cup; top each with a pineapple slice and a cherry.
  3. In a large bowl, beat eggs and sugar until thickened and lemon-colored. Beat in the oil, sour cream and vanilla until smooth. Combine the flour, baking powder, baking soda and salt. Add to egg mixture and mix well.
  4. Fill muffin cups two-thirds full. Bake at 350° for 28-32 minutes or until a toothpick inserted near the center comes out clean. Cool for 5 minutes before inverting onto wire racks to cool completely. Garnish with whipped topping if desired. Yield: 1 dozen jumbo cupcakes.
Originally published as Pineapple Upside-Down Cupcakes in Taste of Home April/May 2007, p29

Reviews for Pineapple Upside-Down Cupcakes

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chefgirl_tammy User ID: 8128080 235205
Reviewed Oct. 18, 2015

"These turned out disgusting! I thought 1 cup of oil couldn't be right but did it any way! they didn't raise at all and tasted so horrible I threw them away! what a waste of 2 hours!"

Grammy Debbie User ID: 30612 224290
Reviewed Apr. 6, 2015

"I made these for our Easter brunch and they are delicious! Easier to make than I first thought, too. I made mine in the jumbo muffin pans and called them pineapple upside down muffins. I had enough topping and batter for 13 jumbo muffins which was a nice surprise--a baker's dozen of these is a good thing indeed!"

Taylo User ID: 8226587 222980
Reviewed Mar. 17, 2015

"Very easy for individual servings"

Jenisl User ID: 6929561 222078
Reviewed Mar. 5, 2015

"These are delicious!"

lor726 User ID: 6883529 221493
Reviewed Feb. 27, 2015

"I do make these all the time with the yellow cake mix. I just replace the water it calls for with the pineapple juice from the can. Remember these are JUMBO cupcakes so the nutritional facts will be higher. I always use regular cupcake pans. If you use the pineapple rings you may have to cut them to fit the reg size pans. I have also used pineapple tidbits and crushed pineapple. All work just fine."

Monicashupe User ID: 8178454 220968
Reviewed Feb. 20, 2015

"Love this !!!!!"

sstetzel User ID: 158954 220788
Reviewed Feb. 18, 2015

"NanyCarol you sure can, I use canned in this recipe and it's wonderful."

NanyCarol User ID: 7999191 220705
Reviewed Feb. 17, 2015

"Can you use canned pineapple instead of fresh? I'm diabetic, but I would certainly try 1/2 of one! You don't have to eat the whole recipe!!!"

kanha1995 User ID: 8067272 220703
Reviewed Feb. 17, 2015

"Wonderful cupcakes. Proud to serve to guests. For those people complaining about the sugar and fat, remember these are for dessert not a meal. Just eat one."

Ban123 User ID: 6337281 220637
Reviewed Feb. 16, 2015

"You can also use a yellow cake mix instead, that would cut down on some calories!!"

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