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–+ servings
Pineapple upside down cupcakes on a wire rack.
5 stars (1 rating)

From Scratch Pineapple Upside Down Cupcakes

Prep: 10 minutes
Cook: 18 minutes
Total: 28 minutes
Servings: 12 cupcakes
These Pineapple Upside Down Cupcakes are a fun twist on the classic dessert! The soft and fluffy vanilla cupcakes are topped with juicy pineapple slices and sweet maraschino cherries, all coated in a delicious caramelized brown sugar glaze. Not only do they look beautiful, but they taste incredible!
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Ingredients

  • 20 oz pineapple slices, canned, or pieces (if using slices you need 2 cans)
  • ½ cup unsalted butter
  • ¾ cup brown sugar
  • Maraschino cherries, 1 jar
  • 1 ¼ cup flour, 160g
  • ¾ cup granulated sugar, 150g
  • 1 tsp baking powder
  • ¼ tsp baking soda
  • ½ tsp kosher salt
  • ¾ cup pineapple juice
  • ¼ cup vegetable oil
  • 1 egg
  • 2 tsp vanilla extract, (optional)

Instructions
 

  • Preheat the oven to 350° F and spray a muffin tin with baking spray- preferably one that is made with flour.
  • Pineapple chunks on a paper towel.
    Drain the pineapple can, reserving ¾ cup of juice. Dry the pineapple slices or pieces well.
  • Sugar glaze in a pot.
    In a small pot add the ½ cup unsalted butter and ¾ cup brown sugar and melt over low- medium heat.
  • Glaze in a muffin tin.
    Add 1 tbsp of the brown sugar mixture to the bottom of each muffin tin.
  • If using pineapple slices/rings- add one to the bottom of your muffin tin with a cherry in the middle. My muffin tin was too small for the ring to fit nicely so I cut it into chunks.
  • Pineapple pieces and cherries in the bottom of a muffin tin.
    If using chunks/pieces- use 3-4 pieces around the muffin tin and place a cherry in the center. If they are very chunky slice them in half.
  • Dry ingredients in a glass bowl on a yellow surface.
    In a large mixing bowl combine the 1 ¼ cup all purpose flour, ¾ cup sugar,1 tsp baking powder, ¼ tsp baking soda, and ½ tsp kosher salt and whisk lightly to combine.
  • Wet ingredients in a glass bowl on a yellow surface.
    Next add in the ¾ reserved pineapple juice, 1/4 cup vegetable oil, 1 egg, and 2 tsp vanilla extract if using. Mix until combined but do not over mix.
  • Cupcake batter in a muffin tin.
    Fill each cup ⅔ of the way full. Do not overfill. You may have a small amount of batter left over. Bake for 18 minutes.
  • Pineapple upside down cupcakes in a muffin tin.
    Cool for 10 minutes in the pan then use a knife to go around the edges of each muffin tin.
  • Pineapple upside down cupcakes on a wire rack.
    Set a wire rack over a parchment covered sheet tray and invert the cupcakes onto the wire rack and let cool completely.
  • Top with whipped cream or powdered sugar for garnish (optional).

Notes

You can use pineapple slices or chunks. Some muffin tins are too small to fit the whole slice nicely so you can cut them up or just use chunks instead.
Serving: 1cupcake, Calories: 300kcal, Carbohydrates: 46g, Protein: 2g, Fat: 13g, Saturated Fat: 6g, Polyunsaturated Fat: 3g, Monounsaturated Fat: 3g, Trans Fat: 0.3g, Cholesterol: 34mg, Sodium: 166mg, Potassium: 119mg, Fiber: 1g, Sugar: 34g, Vitamin A: 281IU, Vitamin C: 6mg, Calcium: 47mg, Iron: 1mg
Course: Cupcake, Dessert
Author: Sam Adler
Cuisine: American
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