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Golden pineapple upside-down cupcakes topped with caramelized pineapple rings and glossy maraschino cherries, served on a white plate.

Pineapple Upside Down Cupcakes

This guide teaches you how to make delicious pineapple upside-down cupcakes, a fun twist on a classic dessert.
Cook Time 18 minutes
Course Dessert

Equipment

  • Mixing bowl
  • Spoon or electric mixer
  • Pan
  • Cupcake tins
  • Toothpick
  • Knife or spatula
  • Plate or cupcake liner

Ingredients
  

  • 1 cup Fresh Pineapple diced. Use a ripe pineapple for the best flavor.
  • 1 cup Granulated Sugar Use a good quality granulated sugar.
  • 0.5 cup Brown Sugar packed. Brown sugar adds a nice depth of flavor.
  • 0.5 cup Butter softened. Use unsalted butter for better flavor control.
  • 2 cups Flour all-purpose. Make sure your flour is fresh.
  • 2 Eggs large. Use large eggs at room temperature.
  • 2 teaspoons Baking Powder Check the expiration date on your baking powder.

Instructions
 

  • Heat sugar in a pan over medium heat. Stir gently until it melts and turns brown. This is caramel! Be careful; it's hot.
  • Place pineapple slices in the bottom of your cupcake tins. You can arrange them in a circle, a star, or any fun way you like!
  • Pour the caramel over the pineapple.
  • Carefully add your cupcake batter on top. Bake according to your recipe.
  • Check your cupcakes regularly. They're done when a toothpick comes out clean. Let them cool before removing them from the tins. The pineapple will be on top – yummy!
  • First, mix the wet ingredients. This means combining the softened butter, eggs, and pineapple. Use a mixing bowl and a spoon or electric mixer. Mix until everything is well combined.
  • Next, in a separate bowl, mix the dry ingredients. This includes the flour, sugar, and baking powder. Whisk these together to make sure the baking powder is evenly distributed.
  • Now, gently add the dry ingredients to the wet ingredients. Stir until just combined. Don't overmix! Overmixing makes tough cupcakes. A few lumps are okay.
  • Carefully pour the cupcake batter over the caramelized pineapple in each cupcake tin. Don't pour it too fast; you want to keep the pineapple in place. Fill each tin about two-thirds full, leaving some space for the cupcakes to rise.
  • Bake the cupcakes in a preheated oven at 350°F (175°C) for 18-22 minutes. Check them after 18 minutes. A toothpick inserted into the center should come out clean when they are done. If the toothpick still has batter on it, bake for a few more minutes and check again. Every oven is a little different, so watch them closely.
  • The cupcakes are ready when they are golden brown on top and a toothpick inserted into the center comes out clean. Let the cupcakes cool in the tins for a few minutes before carefully removing them. The caramelized pineapple will be on top! Enjoy your delicious pineapple upside-down cupcakes.
  • Let your cupcakes cool in the muffin tins for a few minutes after baking. This prevents them from breaking when you remove them. They need to cool slightly before inverting. Don't rush this step!
  • Once slightly cool, carefully run a thin knife or spatula around the edges of each cupcake to loosen them from the tin. Place a small plate or cupcake liner upside down on top of each cupcake. Gently flip the tin and plate together. The cupcake should release easily, showing off the delicious pineapple topping.
  • After your cupcakes cool, it’s time for frosting! You can use cream cheese frosting, which is rich and tangy. Vanilla buttercream is another popular choice—it’s sweet and fluffy. A simple glaze made with powdered sugar and milk or juice is also a quick and easy option. Choose your favorite!
  • Once your cupcakes are frosted, get creative with decorations! You can sprinkle colorful sprinkles on top. Use a toothpick to add swirls of different colored frosting. Fresh pineapple chunks make a pretty and tasty garnish. Get creative and have fun with it! Your cupcakes will look as delicious as they taste.
  • Let your cupcakes cool for a few minutes in the pan. This helps prevent them from breaking when you take them out. Then, use a thin knife to carefully loosen the edges. Invert each cupcake onto a plate or paper liner. The delicious pineapple topping will now be on top!
  • For extra-pretty cupcakes, add a swirl of frosting. Sprinkles or a few fresh pineapple chunks also look great. Get creative and have fun decorating!
  • Store your cooled cupcakes in an airtight container at room temperature for up to three days. For longer storage, freeze them.
Keyword Cupcakes, Pineapple, Upside Down