Delicious Pineapple Upside Down Cupcakes

Category: Treats That Make Everything Better

Pour vanilla cake batter over caramelized pineapple and cherries in muffin pans. Bake, flip when still warm, and enjoy pineapple-flavored treats.
Clare Recipes
Updated on Thu, 13 Mar 2025 12:46:01 GMT
Close-up of Pineapple Cupcakes Save
Close-up of Pineapple Cupcakes | recipesclare.com

These pineapple upside down cupcakes are a tried-and-true crowd pleaser. Perfect for potlucks and gatherings, each cupcake delivers an individual serving of caramelized pineapple atop tender cake - no slicing or serving hassles required. The single-portion format ensures everyone gets that perfect ratio of sticky-sweet fruit topping and moist cake beneath.

This recipe consistently impresses even the most discerning dessert critics. The classic combination of caramelized pineapple, maraschino cherries, and buttery cake has a nostalgic appeal that makes these cupcakes a hit at any gathering.

Key Ingredients

  • Canned pineapple rings: These provide consistent size and sweetness, perfect for individual cupcakes.
  • Dark brown sugar: Creates a rich caramel topping with deep molasses notes.
  • Unsalted butter: Essential for proper caramel texture and rich cake flavor.
  • Maraschino cherries: Adds classic color contrast and traditional garnish.
  • Vegetable oil: Keeps the cake extra moist and tender.
Pineapple Upside Down Cupcakes Homemade Save
Pineapple Upside Down Cupcakes Homemade | recipesclare.com

Step-by-Step Instructions

Prepare the topping
Combine melted butter and brown sugar until sandy in texture. Distribute mixture evenly in muffin cups, spreading with the back of a spoon.
Arrange fruit
Place one pineapple ring in each cup over sugar mixture. Center a dried maraschino cherry in each ring.
Make the batter
Thoroughly cream butter and sugar until light and airy. Incorporate eggs individually, then add vanilla extract.
Combine ingredients
Alternate adding dry ingredients and milk, beginning and ending with flour mixture. Gently fold in oil last.
Fill cups
Carefully spoon batter over pineapple to 3/4 full, avoiding disruption of fruit arrangement.
Invert and unmold
After baking, rest for exactly 5 minutes. Invert pan onto cooling rack in one swift motion.

This recipe transforms the classic pineapple upside down cake into perfectly portioned cupcakes. The tradition of caramelized pineapple desserts continues with this modern adaptation that makes sharing and serving a breeze.

Serving Suggestions

These cupcakes shine on their own, but pair beautifully with lightly sweetened whipped cream or a small scoop of vanilla ice cream. The contrast between warm cake and cold toppings creates an elevated dessert experience.

Variations

The recipe adapts well to modifications. Consider adding dark rum to the caramel for depth, or substitute peach slices and cinnamon for the pineapple. Mini versions using pineapple tidbits work for bite-sized treats.

Storage

Best served day-of, but keep loosely covered at room temperature for up to two days. Avoid tight sealing to maintain caramel texture. A brief warming refreshes texture. Not recommended for freezing.

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Easy Pineapple Upside Down Cupcakes | recipesclare.com

Expert Tips

Use a thin knife around edges before inverting. Choose wider muffin tins for better pineapple presentation. Brush cakes with reserved pineapple juice after turning for extra moisture.

This recipe bridges classic dessert tradition with modern convenience. The individual portions offer consistent quality and easy serving, while maintaining the beloved flavors of traditional pineapple upside down cake. The combination of caramelized fruit and tender cake makes these cupcakes an enduring favorite for any occasion.

Recipe FAQs

→ Can I replace the canned pineapple with fresh ones?
Using fresh pineapple isn’t ideal—it’s hard to get the same thickness and sweetness as canned rings. Canned works best!
→ What’s the best way to store these pineapple cupcakes?
You can store them in a sealed container for up to two days at room temperature, or keep them in the fridge for up to five days. Let them come back to room temperature before eating.
→ How can I stop my cupcakes from sticking to the pan?
Turn them out while warm. If they’re stuck, run a knife along the sides and gently tap the pan’s bottom to free them.
→ Is it possible to skip the cherries?
Sure! Leave the cherries out or try other fruits like raspberries or blueberries—it’s all up to you.
→ Can I add extra spices to the recipe?
Definitely! A bit of cinnamon, nutmeg, or even ginger would taste amazing alongside the pineapple flavor.

Mini Pineapple Cakes

Soft cupcakes topped with sweet caramel, pineapple, and cherries, brought together into a bite-sized dessert everyone will crave.

Preparation Time
20 min
Cooking Time
25 min
Total Time
45 min

Category: Sweet Stuff

Skill Level: Intermediate

Cuisine Type: American

Makes: 12 Serves (12 cupcakes)

Dietary Preferences: Vegetarian

Ingredients

→ For the Topping

01 12 slices of canned pineapple, drained
02 1/2 cup packed brown sugar
03 12 cherries from a jar of maraschino
04 1/4 cup butter, melted and unsalted

→ For the Cake Batter

05 1/3 cup butter, softened for mixing
06 1 1/3 cups regular all-purpose flour
07 1/4 cup neutral vegetable oil
08 2/3 cup milk
09 1 cup plain white sugar
10 1 1/2 teaspoons baking powder
11 2 eggs, large size
12 1/2 teaspoon vanilla essence
13 1/4 teaspoon table salt

Steps

Step 01

Heat the oven to 350°F (175°C). Cover the inside of each cup of a 12-cup muffin pan with some butter or oil to keep things from sticking.

Step 02

In a small dish, stir together the melted butter and brown sugar until it feels smooth. Share this mix equally across all muffin cups to make a sugary base.

Step 03

Pop one pineapple slice into each muffin cup right on top of the sugary base. Add a cherry to the center of the pineapple layer in every cup.

Step 04

In a bowl, beat together the softened butter and sugar until it looks fluffy and smooth. Add in one egg at a time, making sure to mix well. Pour in the vanilla and stir. Take another bowl to combine the dry ingredients—flour, baking powder, and salt—and slowly add this to the wet mix, swapping between milk and dry bits. Finally, gently fold in the oil.

Step 05

Fill each muffin tin almost three-quarters full with the batter, covering the pineapple and cherries. Bake for about 20-25 minutes, or until a tester inserted comes out clean.

Step 06

Once out of the oven, leave the cupcakes in the tin for 5 minutes. Then, turn them upside down onto a wire rack while they’re still warm to ensure the caramel topping comes out smoothly. Let them finish cooling entirely before enjoying.

Helpful Notes

  1. Flip the cupcakes onto the rack while still warm. Otherwise, the caramelized portion will stick once it cools.

Required Tools

  • Muffin tin with 12 slots
  • Bowls for mixing
  • Electric hand or stand mixer
  • Cooling rack

Allergen Info

Check each ingredient for potential allergens and seek medical advice if unsure.
  • Includes dairy (milk and butter)
  • Includes eggs
  • Has gluten from flour