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Pineapple Upside Down Cupcakes take everything you love about the classic cake and turn it into perfectly portioned, individual treats, and I made my first batch for Lizzie’s summer birthday when she wanted something retro and sunny. Each one bakes in a jumbo muffin tin with a gooey brown sugar bottom, a pineapple ring, and a cherry, then flips out golden and gorgeous. They are easier to serve than a whole cake and twice as fun. If you love this style, our easy peach upside down cake is a must.
One bite of that caramelized pineapple top over tender vanilla cake and you will want to make these Pineapple Upside Down Cupcakes for every gathering.
Pineapple Upside Down Cupcakes Quick Look
- 🕒 Prep Time: 15 minutes
- 🌡️ Cook Time: 30 minutes
- ⏳ Total Time: 45 minutes
- 🍽️ Serving: 12 cupcakes
- ⚡ Calories: 524kcal
- 🌶️ Flavor Profile: Sweet, buttery, and caramelized with bright pineapple and vanilla
- ✋ Difficulty: Easy, about as simple as our spice cupcakes
Quick Answer
To make Pineapple Upside Down Cupcakes, melt butter with brown sugar and divide it among a greased jumbo muffin tin, then top each with a pineapple ring and a cherry. Cream butter with granulated and brown sugars, beat in eggs, crushed pineapple, and vanilla, then alternate adding cake flour and buttermilk. Divide the batter over the pineapple, bake at 350 degrees for 20 to 25 minutes, cool 10 minutes, then flip them out and serve.
Jump to:
- Pineapple Upside Down Cupcakes Quick Look
- Quick Answer
- Why This Recipe Works
- Why You’ll Love This Recipe
- Key Ingredients
- Variations and Substitutions
- How to Make Pineapple Upside Down Cupcakes
- Recipe Tips & Tricks
- Serving Ideas and Suggestions
- Pineapple Upside Down Cupcakes FAQs
- Other Recommended Easy Cupcake Recipes
- Pineapple Upside Down Cupcakes
Why This Recipe Works
Click to see the technique science
- A jumbo muffin tin makes perfect portions. Baking the batter in a jumbo tin gives you 12 individual cakes that flip out cleanly, no slicing and no fighting over the corner piece.
- The brown sugar sauce caramelizes the top. Melting butter and brown sugar first creates a gooey base that bakes into a glossy, caramelized topping once the cakes are flipped.
- Cake flour keeps them tender. Lower protein cake flour gives these cupcakes a soft, fine, melt in your mouth crumb.
- Crushed pineapple in the batter adds moisture. A little crushed pineapple stirred into the batter keeps the cakes moist and doubles down on that bright pineapple flavor.
- Creaming the butter and sugar builds the rise. Beating them until light and fluffy whips in air for cakes that bake up tall and tender.
- A 10 minute rest helps them release. Letting the cakes sit before flipping lets the caramel set just enough so they slide out of the tin in one beautiful piece.
Why You’ll Love This Recipe
- Individually portioned. Everyone gets their own little cake with a perfect pineapple ring and cherry on top.
- That retro flavor. Caramelized pineapple and a tender vanilla crumb taste like a classic dessert from grandma’s kitchen.
- A party showstopper. They look impressive with zero fuss, just like our pineapple upside down cheesecake.
Key Ingredients
These Pineapple Upside Down Cupcakes use simple baking staples plus pineapple two ways. Here are the key players.
- Pineapple rings and crushed pineapple: The rings sit on top of each cupcake for that classic look, while crushed pineapple in the batter adds moisture and flavor.
- Maraschino cherries: One in the center of each pineapple ring is the iconic finishing touch.
- Cake flour: Its low protein content gives the cupcakes a soft, fine crumb, the same secret behind our classic moist pound cake.
- Butter and brown sugar: Melted together they form the gooey caramel topping, and creamed into the batter they add richness.
- Buttermilk and eggs: Buttermilk keeps the crumb tender and tangy while eggs give structure and lift.
See recipe card for exact quantities.
Variations and Substitutions
These Pineapple Upside Down Cupcakes are easy to customize. Try these ideas.
- Coconut: Add a little shredded coconut to the batter or sprinkle it over the caramel for a tropical twist.
- Rum: Stir a tablespoon of dark rum into the brown sugar sauce for a grown up flavor.
- Spiced: Add a pinch of cinnamon or nutmeg to the batter.
- Standard muffin tin: Use a regular 12 cup tin with smaller pineapple pieces to make 18 to 24 mini cakes.
- Cherry lovers: Tuck a few extra chopped cherries into the batter.
- More cupcakes: If you love a single serve cake, try our almond raspberry cupcakes next.
How to Make Pineapple Upside Down Cupcakes
- Melt the butter and brown sugar in a saucepan until smooth, then divide it among 12 greased jumbo muffin cups.
- Place a pineapple ring over the sauce in each cup and set a maraschino cherry in the center.
- Cream the softened butter, granulated sugar, and brown sugar until light and fluffy, then beat in the eggs one at a time.
- Stir in the crushed pineapple and vanilla, then alternate adding the cake flour mixture and buttermilk until the batter is smooth.
- Divide the batter evenly over the pineapple in each muffin cup.
- Bake at 350 degrees for 20 to 25 minutes until golden, cool 10 minutes, then flip the cakes out and serve.
Recipe Tips & Tricks
- Grease the tin well. A jumbo tin coated with baking spray helps the caramelized tops release cleanly.
- Pat the pineapple dry. Blot the rings so extra juice does not thin out the caramel.
- Do not overmix the batter. Mix just until combined for the most tender crumb.
- Use room temperature ingredients. Room temp eggs and buttermilk blend smoothly for an even rise.
- Rest before flipping. Ten minutes lets the caramel set so the cakes come out in one piece.
- Flip with a sheet tray. Place a tray over the tin, flip together, wait five minutes, then lift the tin away.
Serving Ideas and Suggestions
These Pineapple Upside Down Cupcakes are a dessert table favorite. Serve them warm with a scoop of vanilla ice cream, or set them out next to our pineapple upside down cheesecake for a pineapple themed spread.
For a bigger dessert bar, pair them with our spice cupcakes and a tray of mini cheesecakes so everyone can sample a few.
They are perfect for summer cookouts and potlucks. Round out the table with our peach upside down cake and a bowl of cream cheese pineapple dip for the fruit lovers.
Pineapple Upside Down Cupcakes FAQs
Yes. This recipe is written for a jumbo muffin tin, but you can use a standard 12 cup tin with smaller pieces of pineapple to make 18 to 24 mini Pineapple Upside Down Cupcakes. Reduce the bake time and watch for a clean toothpick.
Let the Pineapple Upside Down Cupcakes rest in the tin for 10 minutes, place a sheet tray on top, then carefully flip the whole thing over. Wait 5 minutes and lift the tin away so the caramel tops release cleanly.
Yes. Bake and flip the Pineapple Upside Down Cupcakes, then store them covered at room temperature for up to two days or in the fridge for up to four. Warm them briefly before serving for that fresh from the oven taste.
Cake flour gives Pineapple Upside Down Cupcakes the softest, most tender crumb. In a pinch you can make a substitute by replacing two tablespoons of each cup of all purpose flour with cornstarch.
Store Pineapple Upside Down Cupcakes in an airtight container at room temperature for up to two days, or refrigerate for up to four days. The caramel tops stay glossy and the cake stays moist thanks to the crushed pineapple.
Yes. Cool the Pineapple Upside Down Cupcakes completely, then wrap and freeze them for up to three months. Thaw at room temperature and warm gently so the caramel softens again.
Looking for more single serve treats? Try our lemon lime angel food cupcakes next.
Pineapple Upside Down Cupcakes
Ingredients
- 4 tablespoons unsalted butter
- ¾ cup light brown sugar packed
- 12 pineapple rings
- 12 maraschino cherries without stems
For the cake:
- 2 ¾ cup cake flour
- 2 teaspoons baking powder
- ½ teaspoon fine sea salt
- 1 cup unsalted butter softened
- 1 cup granulated sugar
- ¾ cup light brown sugar packed
- 4 large eggs room temp
- ½ cup crushed pineapple
- 1 tablespoon vanilla extract
- ¾ cup buttermilk room temp
Instructions
- Preheat the oven to 350°F. Spray 12 sections of a jumbo muffin tin with baking cooking spray, set aside.
- Add the butter and brown sugar to a small saucepan. Whisk constantly until the sugar is melted 3-5 minutes.4 tablespoons unsalted butter, ¾ cup light brown sugar
- Evenly divide the sauce among the 12 sections of the jumbo muffin tin.
- Add a pineapple ring on top of the sauce and place a cherry in the center, repeat with the remaining muffin tin sections. Set aside.12 pineapple rings, 12 maraschino cherries without stems
- In a large bowl, stir together the cake flour, baking powder, and salt, set aside.2 ¾ cup cake flour, 2 teaspoons baking powder, ½ teaspoon fine sea salt
- In the body of a stand mixer with the paddle attachment add the butter, sugar, and brown sugar. Cream together for 3 minutes until light and fluffy.1 cup unsalted butter, 1 cup granulated sugar, ¾ cup light brown sugar
- Add the eggs one at a time, making sure the first one is mixed in before adding the next.4 large eggs
- Stir in the pineapple and vanilla.½ cup crushed pineapple, 1 tablespoon vanilla extract
- Add half of the flour mixture and mix it in.
- Add half of the buttermilk and mix it in. Repeat one more time until fully combined. Scrape down the sides as needed.¾ cup buttermilk
- Divide the batter among the 12 sections of the muffin tin. Bake for 20-25 minutes until golden brown and a toothpick inserted into the center comes out clean.
- Take the cakes out of the oven and let them sit in the tin on the countertop for 10 minutes. Place a sheet tray on top of the tin and carefully flip the tray over with the muffin tin on top. Wait 5 minutes, then lift the muffin tin off the cakes.
- Let cool and serve warm or room temperature.
Notes
- Don’t Overfill: Leave a little room at the top of the muffin cups so your batter doesn’t spill over.
- Use a Butter Knife: If the cakes won’t budge after flipping, run a butter knife around the edges to loosen them, but be gentle—no one wants a split pineapple ring!
- Check for Golden Brown: You’ll know they’re done when the tops (which become the bottoms) are lightly golden brown. A toothpick in the center of the cake should come out clean.
- Cool Before Flipping: Let them rest for about 10 minutes. Flipping too soon can cause hot syrup to run everywhere—ouch!
- Divide Batter Evenly: If you want each cake the same size, use a measuring cup or scoop so you don’t guess and end up with tall or short ones.
- Experiment: This is a classic dessert, but add your flair. Whether it’s fresh pineapple slices or a drizzle of chocolate, it’s your time to shine!
Nutrition
Love This Recipe?
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Nope, use as is
Do you drain the crushed pineapple ?