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A closeup of pineapple cupcakes on a black cooling rack.

Pineapple Upside-Down Cupcakes

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5 from 1 review

  • Total Time: 37 mins
  • Yield: 24 cupcakes


These easy and delicious cupcakes are always a welcomed dessert!


For the topping:

  • 1/2 cup (1 stick) butter
  • 1 cup dark brown sugar
  • 2 teaspoons dark rum
  • 12 maraschino cherries, sliced in half
  • 1 (20 ounce) can pineapple tidbits, reserve juice for cake mix

For the cupcake batter:

  • 1 package yellow cake mix (I used Duncan Heinz Classic Yellow, 16.5 ounce mix)
  • Reserved pineapple juice (should yield 1 cup of juice)
  • 3 large eggs
  • 1/3 cup vegetable oil


  1. Preheat your oven to 350 degrees F.
  2. Grease 2 (12 cup) muffin pans.
  3. In a small saucepan over medium heat, melt butter. Add brown sugar and rum. Bring to a gentle boil and cook for approximately 2 minutes (stirring often), or until thickened. Remove from heat.
  4. Spoon brown sugar mixture evenly into cupcake tins. Place half of a maraschino cherry in the center of each muffin section. Surround with pineapple tidbits.
  5. In a large bowl, beat cake mix, pineapple juice, eggs and oil on low speed for until moistened, about 30 seconds. Beat on medium speed for 2 minutes.
  6. Spoon cake batter over pineapple, filling almost to the top of each tin (mine were about 7/8 full).
  7. Bake 18 to 22 minutes, or until toothpick inserted in the center is removed clean.
  8. Immediately invert onto wire racks and allow to cool.


Adapted from Taste of Home and A Beautiful Mess

  • Prep Time: 15 mins
  • Cook Time: 22 mins
  • Category: Dessert
  • Method: Bake
  • Cuisine: American