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–+ servings
Pineapple upside down cupcakes on a wire rack.
5 stars (3 ratings)

From Scratch Pineapple Upside Down Cupcakes

These Pineapple Upside Down Cupcakes come together in just 30 minutes, but they look like they took way more effort than that. Canned pineapple is the real star here, bringing that sweet, tangy flavor you can't get any other way. After making these I noticed a few things make or break the result: pat the pineapple completely dry before it goes in the tin, or the extra moisture will make the cupcakes soggy instead of tender. And don't skip the 10 minute cool-down in the pan before flipping; that's what gives the glaze time to set so it releases clean instead of falling apart. These are easier to make than they look!

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.
  • Drain the pineapple can, reserving ¾ cup of juice. Dry the pineapple slices or pieces well.
  • In a small pot add the ½ cup unsalted butter and ¾ cup brown sugar and melt over low- medium heat.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • Cool for 10 minutes in the pan then use a knife to go around the edges of each muffin tin.
  • 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.

STORAGE AND FREEZING

Storing: Store in an airtight container at room temperature for up to 3 days. If you want to keep them fresh for longer, you can store them in the refrigerator for up to 5 days. To maintain their freshness, store them in a container with a tight-fitting lid.
Freezing: These cupcakes can be frozen for up to 3 months. Freeze each cupcake individually in plastic wrap and then place them in a freezer-safe container or freezer bag. When you're ready to eat them, remove them from the freezer and let them thaw at room temperature for a few hours before serving.
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
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