Gluten Free Pineapple Upside Down Cupcakes

If you love classic pineapple upside down cake, these Gluten Free Pineapple Upside Down Cupcakes are going to become a favorite! They have all the nostalgic flavors of the traditional dessert- buttery brown sugar topping, sweet pineapple, and soft vanilla cake, but baked into individual cupcakes that are perfect for parties, summer gatherings, birthdays, or just an easy weeknight dessert.

Why You'll Love These Gluten Free Pineapple Upside Down Cupcakes

These cupcakes are soft, fluffy, and incredibly easy to make, even if you're new to gluten free baking.

The best part? This recipe starts with a gluten free vanilla cake mix, which keeps the process super simple while still giving you bakery-style results. The crushed pineapple adds moisture and sweetness, while the caramelized topping creates that classic pineapple upside down flavor everyone loves.

• Made with a simple gluten free cake mix
• Easy recipe with minimal prep
• Perfect individual-sized desserts
• Moist and fluffy texture
• Great for holidays, BBQs, and summer parties
• Naturally nostalgic!

Unlike some gluten free desserts that can turn out dry or crumbly, the crushed pineapple keeps these cupcakes soft and tender. They also look impressive without requiring any complicated decorating.

Ingredients You'll Need to Make this Gluten Free Pineapple Upside Down Cupcakes Recipe

For the topping:

• Brown sugar
• Butter
• Crushed pineapple
• Maraschino Cherries

For the cupcakes:

• Gluten free vanilla cake mix
• Eggs
• Oil
• Pineapple juice

Best Gluten Free Cake Mixes for these Cupcakes

Almost any quality gluten free vanilla cake mix works well in this recipe!

Some popular options include:

• King Arthur Gluten Free Vanilla Cake Mix- This is what I used!
• Pillsbury Gluten Free Funfetti or Yellow Cake Mix

The pineapple helps create a moist crumb regardless of which mix you choose!

Can I use fresh pineapple?

Canned crushed pineapple gives the best moisture and texture for this recipe.

Love this easy gluten free dessert recipe? I think you'll also love this Easy Gluten Free Peach Cobbler Skillet Recipe and this Gluten Free Strawberry Crisp (Made Without Oats)

How to Make Gluten Free Upside Down Cupcakes

Step 1: Prepare the muffin pan

Preheat your oven to 350°F and grease the cupcake pans well.

In each cupcake cavity, add a teaspoon of butter into the bottom of each muffin cup. Then spoon one tablespoon brown sugar in each cup. Press a cherry into the center of brown sugar in each cup. Spoon a heaping tablespoon of crushed pineapple over the cherry and press it with the back of a spoon into an even layer.

This creates the caramelized upside down topping once the cupcakes are flipped after baking.

Step 2: Make the cake batter

Prepare the gluten free vanilla cake mix, eggs, pineapple juice and oil in a ;arge bowl. Mix until well combined and moistened.

Step 3: Fill and bake

Spoon the batter over the pineapple mixture, filling each cupcake cavity almost full.

Bake for about 18-22 minutes or until a toothpick inserted into the center comes out clean.

Step 4: Cool and flip

Allow the cupcakes to cool for about 5 minutes before carefully flipping them upside down onto a wax paper lined baking sheet.

The warm pineapple topping will settle beautifully over each cupcake.

Easy Variations for this easy Pineapple Upside Down Cupcakes Recipe

Make the cupcakes dairy free

Use your favorite gluten free and dairy free cake mix. Sub the butter in the topping for a vegan version and the rest of the ingredients are already dairy free!

Add coconut

A sprinkle of shredded coconut in the topping gives these cupcakes a tropical twist.

How to Store Gluten Free Pineapple Upside Down Cupcakes

Store leftover cupcakes in an airtight container at room temperature for up to 2 days or refrigerate for up to 5 days.

Because of the pineapple, these cupcakes stay surprisingly moist even after refrigeration.

You can also freeze them for up to 2 months. Just thaw at room temperature before serving.

These easy Gluten Free Pineapple Upside Down Cupcakes are one of those desserts that feel special while being incredibly simple to make. Using a gluten free vanilla cake mix keeps the recipe approachable, while the crushed pineapple and brown sugar topping create that classic homemade flavor everyone loves.

They're soft, buttery, sweet, and perfect for when you want an easy gluten free dessert that still feels nostalgic and impressive.

Whether you're making them for a family gathering, summer party, or just because you're craving pineapple upside down cake, these cupcakes are guaranteed to disappear fast.

Have you tried this recipe? Be sure to leave a comment below and tag me on Instagram @thrivingglutenfree so I can see how it turned out!

Let's Bake!