There’s something magical about the classic pineapple upside-down cake that brings back memories of family gatherings and comfort food. I’ve taken this beloved dessert and transformed it into adorable, perfectly portioned cupcakes that deliver all the nostalgic flavor in a fun, individual serving. These Easy Pineapple Upside Down Cupcakes feature that signature caramelized brown sugar topping, sweet pineapple rings, and maraschino cherries that make the original so irresistible.
What makes these cupcakes special is how they maintain the “wow” factor of flipping them over to reveal that gorgeous, glossy top, but in a much more manageable size. Perfect for potlucks, family desserts, or when you just need a little something sweet, these cupcakes come together in under an hour but taste like you spent all day in the kitchen.
Why You’ll Love This
- Perfect individual portions mean no messy slicing and everyone gets their own caramelized pineapple top
- Much quicker to make than a traditional pineapple upside-down cake
- Uses simple pantry staples and canned pineapple, so you can make them anytime
- The buttery brown sugar topping creates a self-saucing effect that keeps the cupcakes moist
- Makes an impressive presentation with minimal effort
Ingredients
- 1/4 cup unsalted butter, melted
- 1/2 cup brown sugar
- 12 pineapple rings from a can, drained
- 12 maraschino cherries
- 1 1/3 cups all-purpose flour
- 1 cup granulated sugar
- 1/3 cup unsalted butter, softened
- 2/3 cup milk
- 1/4 cup vegetable oil
- 1 1/2 teaspoons baking powder
- 1/2 teaspoon vanilla extract
- 2 large eggs
- 1/4 teaspoon salt
Instructions
- Preheat your oven to 350°F (175°C). Grease a 12-cup muffin tin thoroughly to prevent sticking.
- Mix melted butter and brown sugar in a small bowl until well combined. Divide this mixture evenly among the muffin cups to create a caramel base.
- Place a pineapple ring in each muffin cup on top of the sugar mixture. Add a maraschino cherry in the center of each pineapple ring.
- Beat softened butter and granulated sugar until creamy and light. Add eggs one at a time, mixing well after each. Stir in vanilla. In a separate bowl, whisk together flour, baking powder, and salt. Alternately add dry ingredients and milk to the butter mixture, beginning and ending with flour. Gently fold in the vegetable oil.
- Spoon the batter over the pineapple and cherries, filling each cup about 3/4 full. Bake for 20-25 minutes until a toothpick inserted in the center comes out clean.
- Allow cupcakes to cool in the pan for 5 minutes, then carefully invert onto a wire rack while still warm to ensure the caramelized topping releases cleanly. Let cool completely before serving.
Tips & Variations
- For a more homemade approach, use your favorite vanilla cake recipe instead of boxed mix
- Add 1/2 teaspoon of cinnamon or 1 tablespoon of rum to the batter for a flavor twist
- Use pineapple tidbits instead of rings if that’s what you have on hand
- Try using crushed pineapple (well-drained) for a different texture
- For a tropical variation, add 1/2 cup shredded coconut to the batter
- If you don’t have maraschino cherries, you can omit them or substitute with blueberries
Serving Suggestions
These cupcakes are delicious on their own, but for an extra special treat, serve them slightly warm with a scoop of vanilla ice cream on the side. The contrast between the warm, caramelized cupcake and cold ice cream is absolutely divine!
For a brunch setting, pair these with a cup of coffee or a tropical fruit salad to complement the pineapple flavor. They also make a lovely dessert after a Hawaiian or tropical-themed dinner.
Notes
- Store in an airtight container at room temperature for up to 2 days or refrigerate for up to 5 days
- These cupcakes are best served the same day they’re made, when the topping is at its most caramelized
- If your cupcakes stick to the pan, run a knife around the edges before flipping
- The cupcakes are done when they spring back lightly when touched and a toothpick comes out clean
FAQs
Can I make these cupcakes ahead of time?
Yes, you can make them up to a day ahead, but they’re best enjoyed the day they’re baked when the caramelized topping is fresh.
Can I freeze pineapple upside-down cupcakes?
While possible, freezing isn’t ideal as the texture of the pineapple and the moisture in the topping can change upon thawing. If you must freeze them, wrap individually and thaw completely before serving.
What if I don’t have a muffin tin?
You can use ramekins instead, or make one large cake in a 9×13 inch pan (increase baking time to 30-35 minutes).
Why did my topping stick to the pan?
Make sure to generously grease the muffin tin and flip the cupcakes while they’re still warm (about 5 minutes after removing from the oven).
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