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Pineapple Upside Down Cupcakes – Match Foodie Finds


These Pineapple Coconut Upside Down Cupcakes take a classic and turn it into a tropical delight of caramelized pineapples and moist coconut cake.

Shredded coconut and coconut oil infuse the white cake with a sweet and nutty flavor while caramelizing the pineapple mellows out its natural tartness. Pair that with the brown sugar and almond extract for a delightful summertime treat. These cupcakes are SO yummy 😍

While you’re probably used to seeing this as a sheet cake (peep our Upside Down Peach Cake!), I LOVE the way it looks like cupcakes with a chunk of pineapple crowning each one!

Not gonna lie, it also makes the cake a little easier to handle as it is a little sticky from all that yummy carmelized pineapple, so no worries about slicing and storing these little pieces of heaven. 

These upside-down cupcakes are bursting with flavor. I used pineapple juice instead of water for the cake mix, so you get that tart and sweet flavor in every bite. This cake is just as easy to make as a box mix, so don’t worry about a thing.

Just follow the directions, don’t overmix, and remember to flip the cupcakes as soon as you take them out of the oven. 

  • Unsweetened Shredded Coconut: Little bites of coconut pepper on the cake for a lovely texture and flavor. 
  • Coconut Oil: Instead of butter, you’ll use coconut oil to add fat and a subtle coconut flavor!  
  • Almond Extract: This extract amplifies the nutty flavors of the coconut. 
  • Pineapple Juice: Using the pineapple juice instead of water infuses your batter with tropical flavor! 
  • Eggs: Adds structure and moisture while also working as a leavening agent for a fluffy cake. 
  • Brown sugar: You’ll toss the pineapple chunks in this for subtle sweetness.  
  • Pineapple chunks: They’re the literal crowning achievement of these cupcakes! 
A muffin tin containing evenly chopped apples in each compartment, set on a light textured surface.

For this recipe, we used one 20-oz. can of Del Monte pineapple chunks, which was enough for the pineapple juice and chunks needed. We recommend using canned pineapple instead of fresh, as canned pineapple is softer and has a better texture for the cake. 

Since we used pineapple chunks instead of rings for the topping, we omitted the maraschino cherries, but that doesn’t mean you have to! You can use rings and pop a cherry in the center if you want that super classic look. 

Plate of pineapple upside-down mini cakes topped with pineapple chunks on a light textured surface.

How to Make Pineapple Upside Down Cupcakes

  1. Preheat Oven: Preheat the oven to 350℉ and spray a muffin tin with cooking spray. Set aside.
  2. Mix Dry Ingredients: Add all the dry ingredients to a bowl and whisk together. Set aside. 
  3. Cream Sugar & Oil: Next, add the coconut oil to a large bowl and beat it with an electric mixer on high until smooth. Add the sugar and almond extract to the coconut oil and mix until the mixture is light and fluffy. 
  4. Add Pineapple Juice & Eggs: Slowly pour the pineapple juice into the coconut oil mixture and mix on low. This will not become a homogenous mixture; the coconut oil will slightly congeal, but that is okay. Add one egg at a time until the eggs are just combined.
  5. Mix Wet & Dry: Slowly add the dry ingredients to the wet ingredients, scraping the sides of the mixing bowl a few times. Set aside. 
  6. Assemble: Toss the pineapple chunks with the brown sugar. Then, place one tablespoon of pineapple into each muffin well. Scoop three heaping tablespoons of batter into each muffin cup. 
  7. Bake: Bake for 18-22 minutes or until a toothpick inserted comes out clean. 
  8. Serve & Enjoy: Allow the cupcakes to cool for 5 minutes before flipping them out of the pan. Serve and enjoy!
Close-up of a pineapple upside-down cake topped with whipped cream and pineapple chunks on a white plate.

Don’t overmix! Baked goods are temperamental, and overmixing can cause them to become dry and tough. 

These cupcakes should be stored in the refrigerator to maintain their texture and moistness. They’ll be good for up to 3 days after baking, so you can enjoy them for the entire weekend!

Close-up of a pineapple upside-down cake with a dollop of whipped cream on top, served on a white plate.

Pineapple Coconut Upside Down Cake Pairings

This super sticky and sweet cake is delicious served as is, but you can serve it warm from the oven with our Cookie Dough Banana Nice Cream or homemade Whipped Cream for a delicious take on å la mode.

The fruity flavors of these cupcakes pair well with dessert wines like Moscato, semi-dry wines like Riesling, and most sparkling wines!

  • Preheat the oven to 350℉ and spray a muffin tin with cooking spray. Set aside.

  • Add all of the dry ingredients to a bowl and whisk the ingredients together. Set aside.

  • Next, add the coconut oil to a large bowl and beat it with an electric mixer. Mix on high until the coconut oil is smooth. Add the sugar and almond extract to the coconut oil and mix until the mixture is light and fluffy.

  • Slowly pour the pineapple juice into the coconut oil and sugar mixture and mix on low. This will not become a homogenous mixture, the coconut oil will slightly congeal, but that ok.

  • Add 1 egg at a time until the egg is just combined into the mixture.

  • Slowly add the dry ingredients to the wet ingredients on low and scrape the sides of the mixing bowl a few times. Set aside.

  • Toss the pineapple chunks with the brown sugar. Then, place 1 tablespoon of pineapple into each muffin well.

  • Scoop 3 heaping tablespoons of batter into each muffin cup.

  • Bake for 18-22 minutes or until a toothpick inserted comes out clean.

  • Allow the cupcakes to cool for 5 minutes before flipping them out of the pan.

  • Carmelization of the pineapple will vary depending on what kind of pan you use.
  • We recommend using canned pineapple in this recipe. It is much softer than fresh.
  • For this recipe we used 1- 20 oz. can of del monte pineapple chunks and that was enough for the pineapple juice and chunks needed.

Calories: 209 kcal, Carbohydrates: 32 g, Protein: 3 g, Fat: 9 g, Fiber: 1 g, Sugar: 18 g

Nutrition information is automatically calculated, so should only be used as an approximation.

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