Pineapple upside down cupcakes are a fun, individual twist on the classic pineapple upside down cake. They’re moist, sweet, buttery, and topped with caramelized pineapple and cherries—perfect for parties, holidays, or a quick dessert craving. The best part? They’re incredibly simple to make and look beautiful right out of the pan.
Here’s your easy, foolproof Pineapple Upside Down Cupcakes recipe!
🍍 Ingredients
Topping
⅓ cup butter (melted)
⅔ cup brown sugar
12 pineapple rings (or tidbits)
12 maraschino cherries
Cupcake Batter
You can use a yellow cake mix or make homemade batter.
If using cake mix:
1 box yellow cake mix
Ingredients on the box (usually eggs, oil, water)
Replace ½ of the water with pineapple juice for extra flavor
Homemade Batter Option:
1 ½ cups all-purpose flour
1 cup sugar
1 ½ tsp baking powder
½ cup butter (softened)
2 eggs
½ cup milk
½ cup pineapple juice
1 tsp vanilla extract
👩🍳 Instructions
1. Preheat the Oven
Set your oven to 350°F (175°C).
Lightly spray a 12-cup muffin pan with nonstick spray.
2. Create the Topping
Combine melted butter and brown sugar.
Add about 1 tablespoon of the mixture to the bottom of each muffin cup.
Place 1 pineapple ring (cut to fit) or a spoonful of tidbits on top.
Add one cherry in the center.
This creates the signature sticky, caramelized top of the cupcake.
3. Mix the Cupcake Batter
If using cake mix:
Prepare according to the box, substituting some water with pineapple juice.
If making homemade:
Mix dry ingredients: flour, sugar, baking powder.
Add butter, milk, pineapple juice, vanilla, and mix until smooth.
Add eggs and beat for 1–2 minutes until light and fluffy.
4. Fill the Muffin Cups
Pour batter over the pineapple mixture, filling each cup about ¾ full.
5. Bake
Bake for 18–22 minutes, or until a toothpick comes out clean.
Let cupcakes cool for 5 minutes, then run a knife around the edges.
6. Flip the Cupcakes
Place a baking sheet over the muffin pan and carefully invert.
Lift the pan slowly—your cupcakes should release beautifully, with caramelized pineapple and cherries glistening on top.
⭐ Tips for Perfect Pineapple Upside Down Cupcakes
Use pineapple juice in the batter for extra tropical flavor.
Don’t overfill the muffin cups—they rise quite a bit.
Let them rest 5–10 minutes before flipping—too soon and they fall apart, too late and they stick.
If cupcakes stick, gently tap the bottom of the pan.
Use tidbits if you want more pineapple in each bite.
Add a pinch of cinnamon to the brown sugar topping for a warm twist.
🍒 Fun Variations
Mini Pineapple Upside Down Bites
Use a mini muffin tin with small pineapple chunks—perfect for parties.
Coconut Version
Add ½ cup shredded coconut to the batter.
Cherry-Lovers Cupcakes
Add chopped maraschino cherries to the batter itself.
Spiced Pineapple Upside Down Cupcakes
Add:
½ tsp cinnamon
⅛ tsp nutmeg
🍥 Serving Ideas
These cupcakes are delicious on their own, but you can make them extra special with:
A dollop of whipped cream
A scoop of vanilla ice cream
A drizzle of caramel sauce
Toasted coconut flakes on top
🧊 How to Store
Room Temperature
Store in a covered container for 1–2 days.
Refrigerator
Keeps up to 4 days—warm for 10 seconds before eating.
Freezer
Freeze individually wrapped cupcakes for up to 2 months.