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Pineapple Upside Down Cupcakes

Welcome to the world of baking where tropical flavors meet classic comfort! Today, we’re diving into a delightful recipe that will transport your taste buds to a sunny paradise – Pineapple Upside Down Cupcakes. This recipe is not just about the perfect blend of sweet and tangy flavors, but it’s also about creating a dessert that’s visually appealing and perfect for any occasion.

Easy and Delicious Pineapple Upside Down Cupcakes – Family Favorite Recipe

Every bite of these Pineapple Upside Down Cupcakes takes me back to my grandmother’s kitchen, where the aroma of sweet pineapple and cherries filled the air. It was her secret weapon for bringing the family together, and now, I’m sharing this treasured recipe with you.

The Secrets Behind the Perfect Recipe:

Creating the perfect Pineapple Upside Down Cupcakes is as much about the technique as it is about the ingredients. Here are some secrets that will help you elevate this classic dessert to new heights:

Quality of Ingredients: Always choose the best quality ingredients you can find. For instance, using a high-quality brown sugar can make a significant difference in the caramelization process, enhancing the flavor.
Butter and Brown Sugar Ratio: The key to the perfect caramelized topping lies in getting the ratio of butter to brown sugar just right. Too much butter can make it greasy, while too little won’t allow the sugar to caramelize properly.
Pineapple Placement: Arrange the pineapple and cherries in a visually appealing pattern. This not only makes the cupcakes look more enticing when inverted but also ensures an even distribution of fruit in each bite.
Even Baking: Ensure your oven is properly preheated and bake the cupcakes in the middle rack to promote even cooking. An oven thermometer can help in checking the accuracy of your oven’s temperature settings.
Don’t Overmix the Batter: Mix the batter just until the ingredients are combined. Overmixing can lead to tough cupcakes because it develops the gluten in the flour.
Moisture Content: The crushed pineapple adds moisture to the cupcakes, making them tender. Be sure to drain the pineapple well, but don’t squeeze out all the juice – some moisture is necessary for the perfect texture.
Cooling Time: Allow the cupcakes to cool for just a few minutes before inverting them onto a plate. If they cool too much, they might stick to the pan, but if you invert them too soon, they might fall apart.
Use the Right Tools: A scoop can help you evenly distribute the batter into the cupcake tins, and a thin knife or spatula can help loosen the edges when inverting the cupcakes.
Ingredient Temperature: Ingredients like eggs and butter should be at room temperature to mix evenly and create a smooth batter.
Experiment with Flavors: While the classic recipe is fantastic, don’t be afraid to add your twist, like a sprinkle of cinnamon or a dash of rum for an extra flavor layer.

Remember, baking is both an art and a science. While these tips can guide you, don’t be afraid to trust your instincts and make adjustments based on your preferences and oven peculiarities. Happy baking!

Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes

Recipe by Alexandra
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  • Cooking spray

  • 1/2 cup 1/2 melted butter

  • 1 1/2 cups 1 1/2 brown sugar

  • 24 24 maraschino cherries

  • 1 1 can crushed pineapple

  • 1 1 package pineapple cake mix (such as Duncan Hines® Pineapple Supreme)

  • 3 3 eggs

  • 1 1/3 cups 1 1/3 pineapple juice

  • 1/3 cup 1/3 vegetable oil

  • 1 tablespoon 1 confectioners’ sugar for dusting (optional)


  • Preparation: Preheat your oven to 350 degrees F (175 degrees C). Generously spray your cupcake tins with cooking spray.
  • Creating the Base: In each cupcake tin, place a teaspoon of melted butter, followed by a tablespoon of brown sugar. Add a maraschino cherry in the center and surround it with crushed pineapple.
  • Mixing the Batter: In a large bowl, combine the pineapple cake mix, eggs, pineapple juice, and vegetable oil. Mix until the batter is smooth and free of lumps.
  • Assembling the Cupcakes: Pour the batter over the pineapple and cherry base in each cupcake tin, filling them about three-quarters full.
  • Baking Time: Bake in the preheated oven for about 25 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
  • Finishing Touch: Allow the cupcakes to cool for a few minutes, then carefully invert them onto a serving tray. Dust with confectioners’ sugar for an extra touch of sweetness.

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