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Dessert / Easy Pineapple Upside Down Cupcakes Recipe

Easy Pineapple Upside Down Cupcakes Recipe

February 1, 2026 by LaurenDessert

Easy Pineapple Upside Down Cupcakes are a delightful explosion of tropical sunshine and sweet, caramelized goodness, all baked into a perfectly portioned treat. Who doesn’t adore the classic charm of a pineapple upside down cake? It’s a nostalgic favorite for so many, conjuring up memories of family gatherings and comforting desserts. What truly sets these easy pineapple upside down cupcakes apart is their miniature perfection. You get all the iconic flavors – the tangy sweetness of pineapple, the rich buttery caramel, and the tender cake crum extractb – without the need to slice and serve a whole cake. They’re ideal for parties, picnics, or simply when you crave a burst of cheerful flavor. This recipe transforms the beloved dessert into an accessible and incredibly satisfying cupcake experience, proving that a touch of magic can be baked right into a small, sweet package.

Easy Pineapple Upside Down Cupcakes Recipe

Ingredients:

  • 1/4 cup unsalted butter, melted
  • 1/2 cup packed brown sugar
  • 12 pineapple rings from a can, drained (reserve the juice for another use if desired)
  • 12 maraschino cherries
  • 1 1/3 cups all-purpose flour
  • 1 cup granulated sugar
  • 1/3 cup unsalted butter, softened
  • 2/3 cup milk
  • 1/4 cup vegetable oil
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon vanilla extract
  • 2 large eggs
  • 1/4 teaspoon salt

Preparing the Upside-Down Topping

This is where the magic of the “upside-down” really begin extracts! We’re creating that beautiful, caramelized pineapple and cherry layer that will end up on top of your cupcakes once they’re inverted.

Step 1: Melt the Butter and Mix the Brown Sugar

In a small bowl, combine the 1/4 cup of melted unsalted butter with the 1/2 cup of packed brown sugar. Stir this mixture together until it’s well combined and forms a thick, paste-like consistency. This will be the base for our caramel topping.

Step 2: Assemble the Pineapple and Cherries in Your Muffin Tin

We’ll be doing this step directly in our prepared muffin tin. If you’re using a standard 12-cup muffin tin, make sure it’s greased and floured, or lined with cupcake liners. Spoon about a teaspoon of the brown sugar and butter mixture into the bottom of each muffin cup. Then, place one drained pineapple ring into each cup, pressing it down gently into the sugary mixture. Finally, nestle one maraschino cherry right in the center of each pineapple ring. The goal here is to create a beautiful visual as well as a delicious topping.

Making the Cupcake Batter

Now for the cupcake batter itself! This recipe yields a light and fluffy cake that perfectly complements the sweet pineapple topping.

Step 3: Combine Dry Ingredients

In a medium-sized bowl, whisk together the 1 1/3 cups of all-purpose flour, 1 1/2 teaspoons of baking powder, and 1/4 teaspoon of salt. Whisking these dry ingredients together thoroughly ensures that the leavening agent (baking powder) and salt are evenly distributed throughout the flour. This is crucial for an even rise and consistent flavor in your cupcakes. Set this bowl aside for now.

Step 4: Cream Butter and Sugar, Then Add Wet Ingredients

In a separate, larger mixing bowl, use an electric mixer (or a sturdy whisk and some elbow grease) to cream together the 1/3 cup of softened unsalted butter and the 1 cup of granulated sugar. Creaming means beating them together until the mixture is light, fluffy, and pnon-alcoholic ale yellow in color. This incorporates air into the batter, which contributes to a tender crum extractb. Once creamed, beat in the 2 large eggs, one at a time, making sure each egg is fully incorporated before adding the next. Then, stir in the 1/4 cup of vegetable oil and the 1/2 teaspoon of vanilla extract until just combined. The vegetable oil adds moisture and tenderness to the cake.

Step 5: Alternate Adding Dry and Wet Ingredients to the Creamed Mixture

Now, we’ll gradually incorporate the dry ingredients from Step 3 and the 2/3 cup of milk into the butter and sugar mixture. Start by adding about a third of the dry ingredients to the wet ingredients and mixing on low speed until just combined. Then, add half of the milk and mix again until just incorporated. Repeat this process: add another third of the dry ingredients, followed by the remaining milk, and finally, the last third of the dry ingredients. Be careful not to overmix the batter. Overmixing can develop the gluten in the flour too much, resulting in tough cupcakes. Mix only until you no longer see streaks of dry flour.

Baking and Finishing Your Cupcakes

The final stages involve filling the muffin tin and baking your delightful Easy Pineapple Upside Down Cupcakes.

Step 6: Fill Muffin Cups and Bake

Carefully spoon the cupcake batter over the pineapple and cherry layer in each muffin cup. Fill each cup about two-thirds full. This will give the cupcakes enough room to rise without overflowing. Preheat your oven to 350 degrees Fahrenheit (175 degrees Celsius). Place the filled muffin tin on a baking sheet (this catches any potential drips) and bake for 20-25 minutes, or until a toothpick inserted into the center of a cupcake comes out clean. The aroma of baking caramel and pineapple will fill your kitchen!

Step 7: Cool and Invert

Once baked, remove the muffin tin from the oven and let the cupcakes cool in the tin for about 10 minutes. This brief cooling period allows the caramel to set slightly, making them easier to invert. After 10 minutes, carefully run a thin knife or offset spatula around the edge of each cupcake to loosen it from the pan. Place a wire cooling rack over the top of the muffin tin, and with a confident motion, flip the entire tin and rack over. Gently lift the muffin tin away, revealing your beautiful, caramelized pineapple and cherry topping on each cupcake. If any pineapple or cherries stick to the pan, carefully place them back on top of their respective cupcakes. Let the cupcakes cool completely on the wire rack before serving.

Easy Pineapple Upside Down Cupcakes Recipe

Conclusion:

There you have it – the simple steps to creating delicious and beautiful Easy Pineapple Upside Down Cupcakes! This recipe truly lives up to its name, offering a delightful treat that’s perfect for any occasion, from casual gatherings to a special dessert. The sweet, caramelized pineapple topping combined with a moist, tender cake is a classic combination that never fails to impress. Whether you’re a seasoned baker or just starting out, these cupcakes are incredibly rewarding to make and even more so to enjoy.

For serving, these Easy Pineapple Upside Down Cupcakes are fantastic on their own, but a dollop of whipped cream or a scoop of vanilla ice cream takes them to the next level. They also make a wonderful accompaniment to a cup of coffee or tea. Feel free to experiment with variations! You could add a pinch of cinnamon or nutmeg to the batter for an extra layer of warmth, or even a splash of rum extract to the pineapple mixture for a more grown-up twist. Don’t be afraid to get creative and make them your own. Happy baking!

Frequently Asked Questions:

Can I make these Easy Pineapple Upside Down Cupcakes ahead of time?

Absolutely! These cupcakes can be baked a day in advance and stored in an airtight container at room temperature. For the best texture, it’s recommended to slightly warm them before serving, especially if you’re adding any toppings like whipped cream.

What kind of pineapple should I use for Easy Pineapple Upside Down Cupcakes?

For this recipe, crushed pineapple packed in its own juice is ideal. Draining off some of the excess liquid will help prevent the batter from becoming too wet, ensuring a perfectly baked cupcake. You can also use pineapple rings cut into smaller pieces if you prefer a chunkier topping.

My pineapple topping looks a little dry. What went wrong?

This usually happens if there wasn’t enough liquid in the bottom of the cupcake liners. Ensure you’re using enough melted butter and brown sugar to create a lovely caramel sauce. If it seems dry, you can always drizzle a little extra melted butter and brown sugar mixture over the pineapple before adding the batter.


Easy Pineapple Upside Down Cupcakes Recipe

Easy Pineapple Upside Down Cupcakes Recipe

A simple and delicious recipe for classic pineapple upside down cupcakes, featuring a moist cake and a caramelized pineapple and cherry topping.

Prep Time
20 Minutes

Cook Time
25 Minutes

Total Time
45 Minutes

Servings
12 servings

Ingredients

  • 1/4 cup unsalted butter, melted
  • 1/2 cup packed brown sugar
  • 12 pineapple rings from a can, drained
  • 12 maraschino cherries
  • 1 1/3 cups all-purpose flour
  • 1 cup granulated sugar
  • 1/3 cup unsalted butter, softened
  • 2/3 cup milk
  • 1/4 cup vegetable oil
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon vanilla extract
  • 2 large eggs
  • 1/4 teaspoon salt

Instructions

  1. Step 1
    Prepare the topping: In a small bowl, combine the 1/4 cup melted butter with the 1/2 cup packed brown sugar until a thick paste forms. Spoon about a teaspoon of this mixture into the bottom of each greased and floured muffin cup. Place one drained pineapple ring into each cup, followed by a maraschino cherry in the center.
  2. Step 2
    Combine dry ingredients: In a medium bowl, whisk together the 1 1/3 cups all-purpose flour, 1 1/2 teaspoons baking powder, and 1/4 teaspoon salt. Set aside.
  3. Step 3
    Cream butter and sugar, then add wet ingredients: In a larger bowl, cream together the 1/3 cup softened butter and 1 cup granulated sugar until light and fluffy. Beat in the 2 large eggs one at a time. Stir in the 1/4 cup vegetable oil and 1/2 teaspoon vanilla extract.
  4. Step 4
    Alternate adding dry and wet ingredients: Gradually add the dry ingredients and the 2/3 cup milk to the creamed mixture, alternating between them and mixing until just combined. Do not overmix.
  5. Step 5
    Fill and bake: Spoon the batter evenly into the prepared muffin cups, filling each about two-thirds full. Bake in a preheated oven at 350°F (175°C) for 20-25 minutes, or until a toothpick inserted into the center comes out clean.
  6. Step 6
    Cool and invert: Let the cupcakes cool in the muffin tin for 10 minutes. Carefully run a knife around the edges, then invert the tin onto a wire rack to release the cupcakes. Let cool completely before serving.

Important Information

Nutrition Facts (Per Serving)

It is important to consider this information as approximate and not to use it as definitive health advice.

Allergy Information

Please check ingredients for potential allergens and consult a health professional if in doubt.

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