Pineapple upside down cupcakes are a fun twist on the classic cake, featuring caramelized brown sugar, juicy pineapple, and sweet cherries. This easy recipe uses a cake mix base for convenience while still delivering the familiar buttery, fruity flavor.
A Quick Look at the Recipe
✅ Recipe Name: Pineapple Upside Down Cupcakes
🕒 Ready In: ~35 minutes
👪 Serves: About 12 cupcakes
🥣 Main Ingredients: Pineapple cake mix, sliced pineapple, maraschino cherries, brown sugar, butter, eggs, vegetable oil
👌 Difficulty: Easy - assemble, bake, and flip
⭐ Why You'll Love It: Soft pineapple upside down cupcakes with caramelized brown sugar topping, juicy pineapple, and cherries, made simple with a cake mix base and perfect for individual servings.
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These cupcakes bake up soft and moist with a golden pineapple topping that flips perfectly onto the top of each cupcake. They're simple to assemble, easy to serve, and great for parties, potlucks, or anytime you want a nostalgic dessert in a handheld form.
If you enjoy classic cake flavors, you may also like Chocolate Sheet Cake, Classic Tiramisu, and Apple Cider Cake that are great for sharing.
Jump to:
- A Quick Look at the Recipe
- Why You'll Love Pineapple Upside Down Cupcakes
- Key ingredients
- Easy Substitutions & Variations
- how to make pineapple upside down cupcakes
- Recipe Notes & Tips
- Make-Ahead & Freezing Options
- Pineapple Upside Down Cupcakes faqs
- More Cookie Recipes You'll Love
- Get our Baking Tips & Tricks Ebook
- Pineapple Upside Down Cupcakes
Why You'll Love Pineapple Upside Down Cupcakes
Classic flavor combination: Caramelized brown sugar, pineapple, and cherries create a nostalgic dessert.
Easy cake mix base: Saves time without sacrificing flavor or texture.
Perfect individual servings: Each cupcake flips into its own neat portion.
Soft and moist texture: Pineapple juice keeps the cupcakes tender.
Great for sharing: Ideal for parties, potlucks, and gatherings.
Key ingredients
- Pineapple cake mix: Forms the base of the cupcakes and keeps the recipe quick and reliable.
- Sliced pineapple: Adds juicy, fruity flavor and creates the classic upside down topping.
- Maraschino cherries: Provide sweetness and the signature cherry center on each cupcake.
- Brown sugar: Caramelizes with the butter to form a rich, sticky topping.
- Butter: Melts into the brown sugar to create the classic upside down glaze.
Scroll to the recipe card at the bottom of this page for exact quantities.
Easy Substitutions & Variations
- Homemade cake option: Use a homemade vanilla or yellow cake batter instead of cake mix if preferred.
- Butter swap: Use melted coconut oil in place of butter for a slightly different flavor.
- Fruit variation: Use crushed pineapple or finely chopped pineapple instead of rings for a different texture.
- Cherry option: Swap maraschino cherries for fresh or jarred cocktail cherries if desired.
- Less sweet topping: Reduce the brown sugar slightly if you prefer a lighter caramel flavor.
how to make pineapple upside down cupcakes
- Step 1: Preheat the oven to 350°F and generously grease a standard muffin tin. Spoon a small amount of melted butter into the bottom of each muffin cup, then sprinkle an even layer of brown sugar over the butter.
- Step 2: Drain the pineapple slices, reserving the juice. Cut the pineapple slices into small pieces and divide them evenly among the muffin cups. Place one maraschino cherry in the center of each cup.
- Step 3: In a large mixing bowl, whisk together the vegetable oil, eggs, and reserved pineapple juice until smooth. Add the cake mix and stir just until the batter is evenly combined.
- Step 4: Spoon the batter over the pineapple and cherries, filling each muffin cup about three-quarters full. Bake for 22-25 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
Recipe Notes & Tips
- Grease the pan well: Make sure each muffin cup is generously greased so the cupcakes release cleanly when inverted.
- Use pineapple juice from the can: The reserved pineapple juice adds extra flavor and moisture to the cake batter.
- Do not overfill: Filling the muffin cups about three-quarters full helps prevent overflow while baking.
- Invert while warm: Flip the cupcakes while they are still warm so the brown sugar topping releases easily.
- Cool before serving: Let the cupcakes cool completely so the topping sets and doesn't slide off.
Make-Ahead & Freezing Options
- Make ahead: Pineapple upside down cupcakes can be baked a few hours in advance and kept loosely covered at room temperature until serving.
- Refrigerate if needed: Store leftovers covered in the refrigerator for up to 3 days and bring to room temperature before serving.
- Freeze without topping contact: Freeze fully cooled cupcakes in a single layer, then transfer to an airtight container for up to 2 months.
- Thawing tips: Thaw cupcakes at room temperature until fully softened before serving.
- Best texture note: These cupcakes are best enjoyed fresh, as the topping stays glossy and caramelized.
Pineapple Upside Down Cupcakes faqs
Pineapple upside down cupcakes can stick if the muffin tin is not greased well enough or if they cool too long before flipping. Generously greasing each cup and inverting the cupcakes while they are still warm helps them release cleanly.
Yes, fresh pineapple can be used for pineapple upside down cupcakes. Cut it into small pieces and note that fresh pineapple may be slightly less sweet than canned, so the topping flavor may be a bit more subtle.
Yes, pineapple upside down cupcakes can be made with homemade vanilla or yellow cake batter instead of cake mix. The method stays the same, but bake time may vary slightly depending on the batter used.
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Pineapple Upside Down Cupcakes
Equipment
Ingredients
Instructions
- Preheat the oven to 350°F and generously grease a standard muffin tin.
- Spoon a small amount of melted butter into the bottom of each muffin cup, then sprinkle an even layer of brown sugar over the butter.
- Drain the pineapple slices, reserving the juice. Cut the pineapple slices into small pieces and divide them evenly among the muffin cups. Place one maraschino cherry in the center of each cup.
- In a large mixing bowl, whisk together the vegetable oil, eggs, and reserved pineapple juice until smooth. Add the cake mix and stir just until the batter is evenly combined.
- Spoon the batter over the pineapple and cherries, filling each muffin cup about three-quarters full.
- Bake for 22-25 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
- Remove the pan from the oven and let the cupcakes cool for 5 minutes, then carefully run a knife around the edges and invert the cupcakes onto a wire rack to cool completely.
Nutrition
Notes
- Grease the pan well: Make sure each muffin cup is generously greased so the cupcakes release cleanly when inverted.
- Use pineapple juice from the can: The reserved pineapple juice adds extra flavor and moisture to the cake batter.
- Do not overfill: Filling the muffin cups about three-quarters full helps prevent overflow while baking.
- Invert while warm: Flip the cupcakes while they are still warm so the brown sugar topping releases easily.
- Cool before serving: Let the cupcakes cool completely so the topping sets and doesn't slide off.
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