These Pineapple Upside Down Cupcakes are a delicious homemade dessert with moist cake, pineapple, brown sugar, butter and a cherry on top! Perfect for an everyday dessert, grand-and-go treat or to put out for a party! Plus video tutorial!

Pineapple Upside Down Cupcakes served on a plate

These Pineapple Upside Down Cupcakes are your favorite classic dessert in cupcake form, made from scratch with homemade cake batter, pineapple, brown sugar, butter and a maraschino cherry on top!

They’re delicious as homemade desserts at home, and also to put out for parties and potlucks. We always keep them in mind for Easter, Mother’s Day, Father’s Day and other family gatherings. Don’t forget to pack some for delicious grab-and-go snacks and lunches too.

Pineapple Upside Down Cake is an American classic that became popular with the arrival of canned pineapple in the early 1900s. Now we’ve remade this old-fashioned dessert in cupcake form, and it’s just as moist! The best part? The flavor actually improves with time, so they’re ideal to make ahead of time.

How to Make Pineapple Upside Down Cupcakes

There are 3 easy steps for making pineapple upside down cupcakes:

Steps 1: Prepare the Pan

Prepare a jumbo-size muffin tin by spraying thoroughly with nonstick cooking spray. Then spoon brown sugar and melted butter mixture into each muffin cup. Then add a pineapple ring on top and a maraschino cherry in the middle. Reserve the leftover pineapple juice for the next step.

Pineapple Upside Down Cupcakes preparation showing the pineapple, brown sugar and butter mixture and cherry in a muffin tin

Step 2: Make the Batter

In a medium bowl, make the cake batter by combining the eggs, sugar, pineapple juice, vanilla, flour, baking powder and salt following the recipe. Then pour the batter to fill each muffin cup about half to two-thirds full.

Step 3: Bake and Unmold

Bake for 20-25 minutes at 350°F until golden brown on top and a cake tester or toothpick inserted in the middle comes out clean. Remove from the oven and wait 3-5 minutes. Then place a wire rack on top of the pan and invert. If the cups don’t dislodge right away, bang on the counter a few times to loosen them.

Tips and Secrets for Making Pineapple Upside Down Cupcakes

  • If you can’t find pineapple rings, then use a similar quantity of crushed pineapple chunks instead.
  • If you have to use a smaller muffin pan, use crushed pineapple instead of rings and reduce baking time slightly.
  • These cupcakes will keep for 2-3 days stored in an airtight container, and the flavor will improve with time.
  • For easy unmolding, wait 3-5 minutes after baking before inverting the pan. If you wait much longer, the brown sugar mixture will harden and become difficult to unmold.
  • After unmolding, wait at least 10 minutes before eating as the pineapple will be very hot and it’s easy to burn your mouth.

Watch How to Make Pineapple Upside Down Cupcakes:

See how to make this easy recipe for Pineapple Upside Down Cupcakes
5 from 1 vote

Pineapple Upside Down Cupcakes

These Pineapple Upside Down Cupcakes are a delicious homemade dessert featuring pineapple, brown sugar, butter and a cherry on top! Perfect for an everyday dessert, grand-and-go treat or to put out for a party!
Prep Time: 15 mins
Cook Time: 20 mins
Total Time: 35 mins
Servings: 6 servings


  • 1/4 cup butter
  • 2/3 cup brown sugar
  • 14- oz pineapple rings, canned or fresh
  • 6 maraschino cherries
  • 2 large eggs
  • 2/3 cup sugar
  • 4 tbsp pineapple juice
  • 1 tsp vanilla
  • 2/3 cup flour
  • 1 tsp baking powder
  • 1/4 tsp salt


  • Preheat oven to 350°F. Spray a jumbo size muffin pan thoroughly with nonstick cooking spray.
  • In a small saucepan, melt the butter over medium heat, and whisk in brown sugar until blended.
  • Spoon about 2 tablespoons of topping mixture into each muffin cup, and then place a pineapple ring and cherry on top.
  • In a medium bowl, beat eggs and sugar until smooth. Mix in pineapple juice, vanilla, flour, baking powder and salt.
  • Divide batter evenly across 6 muffin cups and bake for 20-25 min until golden brown. 
  • Remove from oven and cool for 5 min before running a knife around the outside of each cake.
  • Place a cooling rack on top of muffin pan and quickly invert to unmold. Bang on counter to help loosen cakes. Serve and enjoy!


Calories: 367kcal, Carbohydrates: 67g, Protein: 4g, Fat: 10g, Saturated Fat: 6g, Polyunsaturated Fat: 1g, Monounsaturated Fat: 3g, Cholesterol: 92mg, Sodium: 359mg, Potassium: 195mg, Fiber: 1g, Sugar: 56g, Vitamin A: 7%, Vitamin C: 11%, Calcium: 12%, Iron: 9%
Author: TipBuzz
Course: Dessert
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Editor note: Published August 26, 2016 and updated April 2, 2018.