Pineapple Upside Down Cupcakes


Looking for a fun and fruity dessert for your next luau, party or casual gathering? These pineapple upside down cupcakes are sure to be a crowd-pleasing hit! Imagine all the delicious flavors of the classic pineapple upside down cake packed into adorable individual portions. With caramelized brown sugar, buttery pineapple, and a cherry on top, every bite is like a burst of sunshine.

What makes these pineapple cupcakes so irresistible? Let’s start with the sweet and tangy pineapple – the star of the show. Whether you use crushed pineapple or pineapple tidbits, the fruit gets lightly caramelized with brown sugar as the cupcakes bake. The result is concentrated pineapple flavor in every morsel.

Then you have the caramelized brown sugar lending its rich molasses notes along with cherries adding a bright pop of fruity sweetness. It’s all supported by a super moist cake made extra flavorful by using pineapple juice in place of water.

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Why You’ll Love This Pineapple Upside Down Cupcake Recipe:

  • Easy to make starting with a cake mix base
  • Loaded with real pineapple flavor in each bite
  • Pretty presentation with the pineapple and cherry topping
  • Versatile for parties, potlucks, BBQs or casual dessert
  • Can make ahead and enjoy at room temp or warm

Ingredients Needed:

  • Yellow cake mix
  • Eggs and oil (per cake mix instructions)
  • 1 1/3 cups pineapple juice
  • 1/2 cup melted butter
  • 1 1/2 cups brown sugar
  • 20 oz can crushed pineapple (or pineapple tidbits)
  • 24 maraschino cherries
  • Confectioners’ sugar for dusting (optional)

How to Make Pineapple Upside Down Cupcakes:

  1. Prep the pans by spraying cups with nonstick spray. Add 1 tsp melted butter followed by 1 tbsp brown sugar to each cup. Place a cherry in the center and top with pineapple.
  2. Make cake batter as directed on box, using pineapple juice in place of the water.
  3. Divide batter evenly among prepared muffin cups.
  4. Bake at 350°F for 18-22 minutes until a toothpick comes out clean.
  5. Allow to cool for 5 minutes, then invert onto a parchment-lined surface.
  6. Optionally, dust the tops with confectioners’ sugar before serving.

FAQs About These Tropical Cupcakes

What type of pineapple is best to use?
I prefer crushed pineapple for maximum flavor dispersed in every bite. Tidbits can work but may get stuck in tins.

How do I avoid the cupcakes sticking to the pans?
Be sure to grease the pan very well with non-stick spray or butter. Also allow them to cool slightly before inverting.

Can I make these ahead of time?
Yes! Once baked and inverted, the cupcakes stay fresh at room temperature for 2-3 days.

Can you reheat pineapple upside down cupcakes?
You can enjoy these at room temp, or reheat for 10-15 seconds in the microwave to warm them up.

How to Store Leftovers:

Keep any leftover pineapple upside down cupcakes at room temperature in an airtight container for up to 3 days. Optionally, you can refrigerate for up to 1 week.

With their fun compact size and explosion of tropical flavors, these pineapple upside down cupcakes make for a delightful dessert. Easy to whip up with a boxed cake mix shortcut and loaded with fresh pineapple taste! They’re sure to disappear quickly at any backyard BBQ or party. Give this crowd-pleasing recipe a try this summer!

Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes stuffed with crushed pineapple, brown sugar caramel, and a cherry on top! Easy cupcakes made from a cake mix with mega pineapple flavor.
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Course: Dessert
Cuisine: American
Prep Time: 10 minutes
Cook Time: 20 minutes
Total Time: 30 minutes
Servings: 20 Cupcakes


  • Cooking spray
  • 1/2 cup butter melted
  • 1 1/2 cups brown sugar
  • 24 maraschino cherries
  • 20 oz can crushed pineapple reserve juice
  • 15.25 oz package yellow cake mix
  • Vegetable oil and eggs per cake mix instructions
  • 1 1/3 cups pineapple juice
  • Confectioners’ sugar for dusting optional


  • Preheat oven to 350°F and spray 24 muffin cups with cooking spray.
  • Line a surface with parchment paper.
  • Add 1 tsp melted butter to each muffin cup.
  • Add 1 tbsp brown sugar to each cup.
  • Place a cherry in the center of each cup.
  • Top each with a heaping tbsp crushed pineapple.
  • Make cake batter per box instructions, using pineapple juice instead of water.
  • Pour batter into prepared muffin cups, filling almost to the top.
  • Bake for 18-22 minutes until a toothpick inserted comes out clean.
  • Allow to cool 5 minutes, then invert onto the parchment to release.
  • Optionally, dust with confectioners’ sugar before serving.


  • – Use pineapple juice reserved from the crushed pineapple can to replace the water in the cake mix. Add water if needed to meet liquid requirements.
  • – For a pretty presentation, you can use pineapple tidbits instead of crushed pineapple, but the flavor won’t be as strong.


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