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+ servings

Pineapple Upside Down Cupcakes

Moist, flavorful and made with real pineapple juice mixed into the batter, pineapple chunks, whipped cream, cherry and brown sugar caramel.
Course Dessert
Prep Time 20 minutes
Cook Time 24 minutes
Total Time 44 minutes
Servings 12


  • 2 (20 ounce) cans of Pineapple chunks in pineapple juice
  • 1/3 cup light brown sugar
  • 1/3 cup butter , melted
  • 1 cup all-purpose flour - I used White Lily
  • 3/4 cup granulated sugar
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1/4 cup butter , softened
  • 1/2 cup (4 ounces) pineapple juice (from pineapple chunk cans)
  • 1 large egg
  • 1/2 teaspoon vanilla extract
  • 12 maraschino cherries
  • Topping
  • 1 can whipped topping
  • or
  • 3/4 cup heavy cream , cold
  • 2 tablespoons sugars


  • Preheat oven to 350 degrees F. Spray 12 cup cupcake pan with non-stick cooking spray. Open both cans of pineapple chunks and drain liquid into glass and set liquid aside, this will be used for cupcake batter. Layer paper towel and spoon pineapple chunks onto paper towel.
  • In a microwave safe dish, melt butter and stir in brown sugar to dissolve. Using a teaspoon, scoop about 2 teaspoons into each prepared muffin tin. You will want to fit 5 pineapple chunks into each tin. Since the chunks may be different sizes, I used a knife to cut the off a small part of the chunk on the long ends. Arrange in tin like a flower, repeat until done; set aside.
  • In a large bowl fit with a mixer, combine flour, 3/4 cup sugar, salt and baking powder. Add butter and turn mixer on medium speed then pour in pineapple juice. Continue mixing until batter is smooth, about 1 to 2 minutes. Add vanilla extract and egg then keep mixing, wiping batter down from the side of bowl with spatula. Scoop batter over pineapple arrangements in tin. Bake in over for about 23 to 26 minutes or until a toothpick inserted in the center comes out clean.
  • Allow cupcakes to cool completely. Removing too soon can result in muffin falling apart. Once cool, run a clean knife around the edges of cupcakes until it comes out. Place on rack with pineapple side up.
  • To make the whipped topping, pour cream in bowl fit with a whisk attachment. Whip cream on high speed until soft peaks form. Add sugar and whip until cream is stiff.
  • Assemble cupcakes just before serving. Pipe whipped cream/spray can over the top of cupcake and place cherry on top. Also, I made extra brown sugar and melted butter mix and spooned it over the top before the whipped cream was added.