Name: From Scratch Pineapple Upside Down Cupcakes Recipe
Prep time: 15 min
Cook time: 18 min
Total time: 33 min
Cuisine: American
Ingredients: 20 oz pineapple slices (canned, or pieces; if using slices you need 2 cans); ½ cup unsalted butter; ¾ cup brown sugar; Maraschino cherries (1 jar); 1 ¼ cup all-purpose flour (160g); ¾ cup granulated sugar (150g); 1 tsp baking powder; ¼ tsp baking soda; ½ tsp kosher salt; ¾ cup pineapple juice (reserved from canned pineapple); ¼ cup vegetable oil; 1 large egg; 2 tsp vanilla extract (optional)

Jump to Recipe

If you’ve ever swooned over a classic pineapple upside down cake but wished it was portable, individual-sized, and bursting with tropical sweetness, then these From Scratch Pineapple Upside Down Cupcakes are about to become your new obsession. Imagine tender, moist cupcakes with that rich, caramelized pineapple and cherry topping you love, all baked right in your muffin tin for perfectly portioned treats. These cupcakes balance the perfect hint of brown sugar caramel, luscious pineapple, and a soft crumb that will remind you why homemade desserts always win hearts faster than anything store-bought. From the buttery brown sugar base to the hint of vanilla and the delightful pineapple juice infused inside, these cupcakes redefine what it means to enjoy a classic in cupcake form.

From Scratch Pineapple Upside Down Cupcakes Recipe - Recipe Image

Ingredients You’ll Need

These ingredients are wonderfully simple but totally essential for nailing the sweet, moist, and colorful nature of From Scratch Pineapple Upside Down Cupcakes. Each one plays its part—from the caramel richness of brown sugar to the refreshing brightness of fresh pineapple juice and the structural magic of baking powder.

20 oz pineapple slices or pieces: Whether canned slices or chunks, drying them well is key to avoid soggy cupcakes and to concentrate flavor.
½ cup unsalted butter: Provides a glossy, rich caramel base for that signature golden topping.
¾ cup brown sugar: Melts into butter to create the irresistible caramel sweetness that crowns these cupcakes.
Maraschino cherries (1 jar): Classic for that pop of color and a sweet, fruity center atop each cupcake.
1 ¼ cup all purpose flour (160g): The backbone ingredient that ensures fluffy yet sturdy cupcakes.
¾ cup granulated sugar (150g): Sweetens the cake batter, balancing the brown sugar topping perfectly.
1 tsp baking powder: Gives the cupcakes lift and lightness.
¼ tsp baking soda: Works with the acidic pineapple juice to contribute to a tender crumb.
½ tsp kosher salt: Enhances all the sweet flavors and deepens complexity.
¾ cup pineapple juice: Adds natural pineapple flavor and moisture for a juicy cupcake.
¼ cup vegetable oil: Keeps the cupcakes moist and tender without weighing them down.
1 egg: Binds the ingredients together and contributes to the cupcake’s structure.
2 tsp vanilla extract (optional): Adds a subtle warmth and depth to the batter.

How to Make From Scratch Pineapple Upside Down Cupcakes

Step 1: Prepping the Pan and Pineapple

Start by preheating your oven to 350°F and generously spraying a muffin tin with baking spray that contains flour to prevent sticking. Drain your canned pineapple, reserving three-quarters of a cup of the juice to infuse the cupcakes with that lovely tropical flavor. Be sure to pat the pineapple dry because moisture on the fruit can ruin that perfect caramel topping you’re aiming for.

Step 2: Make the Caramel Base

On the stovetop, melt the unsalted butter with the brown sugar in a small pot over low to medium heat. Stir gently until all the sugar dissolves and the mixture is shiny and smooth. This mixture is the secret to that sticky, glossy layer under your cupcakes, so do not rush this step. Spoon one tablespoon of this heavenly caramel into the bottom of each muffin cup.

Step 3: Layering the Pineapple and Cherry

Next, arrange your pineapple slices or pieces on top of the caramel in each muffin cup. If the slices don’t fit your muffin tin, cut them into chunks so they nestle nicely. Add a maraschino cherry in the center for that classic look and fruity burst of flavor. This colorful layer not only looks stunning but melts into the caramel during baking for maximum yum.

Step 4: Mixing the Batter

In a large bowl, whisk together the flour, granulated sugar, baking powder, baking soda, and kosher salt. In a separate bowl, combine the pineapple juice, vegetable oil, egg, and vanilla extract if you’re using it. Pour the wet ingredients into the dry ones and mix gently until just combined. Overmixing can toughen the cupcakes, so be careful.

Step 5: Baking the Cupcakes

Fill each muffin cup about two-thirds full with the batter to leave room for rising. Bake your cupcakes for about 18 minutes, or until a toothpick inserted into the center comes out clean. Once done, let them cool in the pan for around 10 minutes before running a knife around each cupcake to loosen them.

Step 6: The Grand Reveal

Place a wire rack over a parchment-lined sheet tray, then carefully invert the muffin tin so the cupcakes drop out with their glorious pineapple and cherry topping facing up. Cool completely on the rack before serving to let the caramel set.

How to Serve From Scratch Pineapple Upside Down Cupcakes

Garnishes

These cupcakes are stunning on their own, but for a little extra flair, top them with a dollop of whipped cream, a light dusting of powdered sugar, or even a sprinkle of toasted coconut flakes for a tropical twist. The light creaminess or added texture really complements the warm caramelized pineapple.

Side Dishes

Serve these cupcakes alongside a scoop of vanilla ice cream or a refreshing citrus sorbet for a delightful balance of warm and cool. They also pair beautifully with a cup of freshly brewed coffee or a chilled glass of sparkling wine for a celebratory touch.

Creative Ways to Present

For parties, place each cupcake in a colorful cupcake liner that matches your theme. You can also serve them on a wooden board for a rustic feel or arrange them on a tiered cake stand for a wow-worthy dessert display. Individual cupcake boxes make great gifts too!

Make Ahead and Storage

Storing Leftovers

Keep any leftover From Scratch Pineapple Upside Down Cupcakes in an airtight container at room temperature for up to two days to maintain their moisture and texture. If your kitchen is warm, storing them in the refrigerator is fine, but bring them to room temperature before serving for the best taste.

Freezing

These cupcakes freeze wonderfully! Wrap each cupcake individually in plastic wrap and place them in a freezer-safe container or bag. They’ll keep for up to three months. When you’re ready, thaw overnight in the fridge and warm briefly in the microwave or oven if desired.

Reheating

To enjoy the fresh-baked experience, reheat your cupcakes in a 300°F oven for about 5-7 minutes. This brings back that soft, moist texture and revives the caramelized topping’s warm glow without drying them out.

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple works great as long as you drain and pat the pieces dry to avoid excess moisture messing with the caramel topping and cupcake texture.

Do I need to use baking spray with flour?

Yes, it helps prevent the sticky caramel topping from sticking to the pan, ensuring your cupcakes release cleanly and keep their beautiful tops intact.

Can I make these cupcakes vegan or dairy-free?

With some substitutions like plant-based butter and an egg replacer, you can adapt the recipe. Just be mindful that changes might slightly alter the texture and flavor.

What’s the best way to store the cupcakes if I’m not serving them immediately?

Store them in an airtight container, either at room temperature or refrigerated depending on your climate, and avoid exposure to air to keep them from drying out.

Can I double the recipe for a larger batch?

Yes, doubling is straightforward—just make sure to bake in batches or use multiple muffin tins, and adjust baking time slightly if necessary by checking for doneness with a toothpick.

Final Thoughts

Whipping up a batch of From Scratch Pineapple Upside Down Cupcakes isn’t just baking; it’s creating little moments of joy that bring sunshine indoors. Whether you’re making them for a special gathering or a sweet afternoon treat, these cupcakes are bursting with flavor and heartwarming nostalgia. I can’t wait for you to try them and see just how easy and rewarding baking from scratch can be!

From Scratch Pineapple Upside Down Cupcakes Recipe

★★★★★

4.7 from 23 reviews

Author: Ethan
Total Time: 33 minutes
Yield: 12 cupcakes 1x
Diet: Vegetarian

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Description

These From Scratch Pineapple Upside Down Cupcakes are a delightful twist on the classic dessert, offering individual portions with moist vanilla cupcakes topped with caramelized brown sugar, buttery pineapple, and cherries. Perfect for parties or a sweet treat, they combine the tropical tang of pineapple with a rich, buttery topping for a deliciously nostalgic bite-sized dessert.

Instructions

Preheat and Prepare Pan: Preheat your oven to 350° F (175° C) and spray a muffin tin with baking spray containing flour to prevent sticking.
Drain Pineapple: Drain the canned pineapple, setting aside ¾ cup of the juice for the batter. Pat the pineapple slices or pieces dry to remove excess moisture.
Make Caramel Mixture: In a small saucepan over low to medium heat, melt ½ cup unsalted butter and ¾ cup brown sugar together until combined and smooth.
Layer Base: Spoon about 1 tablespoon of the brown sugar and butter mixture into the bottom of each muffin tin cup.
Add Pineapple and Cherries: If using pineapple slices or rings, place one ring at the bottom of each muffin cup and place a maraschino cherry in the center. If rings are too large, cut into chunks. For pineapple chunks, arrange 3-4 pieces around the bottom with a cherry in the center.
Mix Dry Ingredients: In a large bowl, whisk together 1 ¼ cup all-purpose flour, ¾ cup granulated sugar, 1 teaspoon baking powder, ¼ teaspoon baking soda, and ½ teaspoon kosher salt.
Combine Wet Ingredients: Add the reserved ¾ cup pineapple juice, ¼ cup vegetable oil, 1 egg, and 2 teaspoons vanilla extract (optional) to the dry ingredients. Mix gently until all ingredients are just combined, taking care not to overmix.
Fill Muffin Cups: Spoon the batter into each muffin cup, filling them about ⅔ full. Avoid overfilling to prevent spilling and uneven baking.
Bake: Place the muffin tin in the oven and bake for 18 minutes, or until a toothpick inserted in the center comes out clean.
Cool in Pan: Let the cupcakes cool in the pan for about 10 minutes. Then, run a knife around the edges of the muffin cups to loosen the cupcakes.
Invert Cupcakes: Position a wire rack over a parchment-lined sheet tray. Invert the cupcakes onto the wire rack to reveal the pineapple upside down tops. Allow them to cool completely.
Garnish and Serve: Optionally top the cooled cupcakes with whipped cream or a light dusting of powdered sugar before serving for extra sweetness and presentation.

Notes

Make sure to pat the pineapple dry to reduce excess moisture and avoid soggy cupcakes.
Use a muffin pan sprayed with flour-based baking spray to ensure easy removal of cupcakes after baking.
The optional vanilla extract adds depth of flavor but can be omitted if unavailable.
These cupcakes are best enjoyed the same day for optimal texture but can be stored in an airtight container for up to 2 days.
You can substitute vegetable oil with melted coconut oil for a slight tropical twist.
For a gluten-free version, substitute the all-purpose flour with a gluten-free flour blend at a 1:1 ratio.

Prep Time: 15 minutes
Cook Time: 18 minutes
Category: Dessert
Method: Baking
Cuisine: American