Pineapple Upside Down Cupcakes
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These Pineapple Upside Down Cupcakes are a delicious dessert with moist cake, pineapple, brown sugar, butter and a cherry on top!
These Pineapple Upside Down Cupcakes are your favorite classic dessert in cupcake form, made from scratch with homemade cake batter, pineapple, brown sugar, butter and a maraschino cherry on top!
They’re delicious as homemade desserts at home, and also to put out for parties and potlucks. We always keep them in mind for Easter, Mother’s Day, Father’s Day and other family gatherings. Don’t forget to pack some for delicious grab-and-go snacks and lunches too.
How to Make Pineapple Upside Down Cupcakes
There are 3 easy steps for making pineapple upside down cupcakes:
Steps 1: Prepare the Pan
Prepare a jumbo-size muffin tin by spraying thoroughly with nonstick cooking spray. Then spoon brown sugar and melted butter mixture into each muffin cup. Then add a pineapple ring on top and a maraschino cherry in the middle. Reserve the leftover pineapple juice for the next step.
Step 2: Make the Batter
In a medium bowl, make the cake batter by combining the eggs, sugar, pineapple juice, vanilla, flour, baking powder and salt following the recipe. Then pour the batter to fill each muffin cup about half to two-thirds full.
Step 3: Bake and Unmold
Bake for 20-25 minutes at 350°F until golden brown on top and a cake tester or toothpick inserted in the middle comes out clean. Remove from the oven and wait 3-5 minutes. Then place a wire rack on top of the pan and invert. If the cups don’t dislodge right away, bang on the counter a few times to loosen them.
Tips for Making Pineapple Upside Down Cupcakes
- If you can’t find pineapple rings, then use a similar quantity of crushed pineapple chunks instead.
- If you have to use a smaller muffin pan, use crushed pineapple instead of rings and reduce baking time slightly.
- These cupcakes will keep for 2-3 days stored in an airtight container and the flavor improves with time.
- For easy unmolding, wait 3-5 minutes after baking before inverting the pan. If you wait much longer, the brown sugar mixture will harden and become difficult to unmold.
- After unmolding, wait at least 10 minutes before eating as the pineapple will be very hot and it’s easy to burn your mouth.
Recipe Video – Pineapple Upside Down Cupcakes:
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Pineapple Upside Down Cupcakes
- 1/4 cup unsalted butter
- 2/3 cup brown sugar
- 14- oz pineapple rings, canned or fresh
- 6 maraschino cherries, optional
- 2 large eggs
- 2/3 cup sugar
- 4 tbsp pineapple juice
- 1 tsp vanilla
- 2/3 cup flour
- 1 tsp baking powder
- 1/4 tsp salt
- Preheat oven to 350°F. Spray a jumbo size muffin pan thoroughly with nonstick cooking spray.
- In a small saucepan, melt the butter over medium heat, and whisk in brown sugar until blended.
- Spoon about 2 tablespoons of topping mixture into each muffin cup, and then place a pineapple ring and cherry on top.
- In a medium bowl, beat eggs and sugar until smooth. Mix in pineapple juice, vanilla, flour, baking powder and salt.
- Divide batter evenly across 6 muffin cups and bake for 20-25 min until golden brown.
- Remove from oven and cool for 5 min before running a knife around the outside of each cake.
- Place a cooling rack on top of muffin pan and quickly invert to unmold. Bang on counter to help loosen the cakes. Serve warm.
- Ahead of Time Note: You can store these cupcakes in an airtight container in the fridge for up to 3 days or in the freezer for up to 2 months.
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Editor note: Published August 26, 2016 and updated April 2, 2018.