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Pineapple Upside-Down Cupcakes

I have baked cupcakes for years. These easy to make treats make an attractive dessert for special occasions. —Barbara Hahn, Park Hills, Missouri
  • Total Time
    Prep: 30 min. Bake: 30 min. + cooling
  • Makes
    1 dozen jumbo cupcakes


  • 6 tablespoons butter, cubed
  • 1 cup packed light brown sugar
  • 2 tablespoons light corn syrup
  • 12 slices pineapple, drained
  • 12 maraschino cherries, well drained
  • 3 large eggs, room temperature
  • 2 cups sugar
  • 1 cup canola oil
  • 1 cup 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


  • Line the bottom of 12 greased jumbo muffin cups with waxed paper; grease the paper and set aside.
  • 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.
  • 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.
  • Fill muffin cups two-thirds full. Bake at 350° for 28-32 minutes or until a toothpick inserted in the center comes out clean. Cool for 5 minutes before inverting onto wire racks to cool completely. Garnish with whipped topping if desired.

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  • Stephanie Jesus
    Feb 27, 2018

    Very moist cupcakes!!!!!

  • Patricia
    Aug 4, 2017

    I love this recipe! Turned out perfectly. I was out of cherries and didn't want to make a run to the store so I used craisins to sprinkle in with the pineapple...perfect and a great flavor with the pineapple! The cake part was light and just moist enough...

  • chefgirl_tammy
    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
    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
    Mar 17, 2015

    Very easy for individual servings

  • Jenisl
    Mar 5, 2015

    These are delicious!

  • lor726
    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
    Feb 20, 2015

    Love this !!!!!

  • sstetzel
    Feb 18, 2015

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

  • NanyCarol
    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!!!