INTRODUCTION
Pineapple Upside Down Cupcakes bring the charm of the classic cake into a small, fun size. These cupcakes are soft and sweet with a caramelized pineapple at the bottom that becomes the top when you turn them over. They are easy to make and share. You can make them for a weeknight dessert, a picnic, or a small party. If you like simple fruit desserts, you will like these cupcakes. For a fruity twist on other small cakes, see this easy apple cupcakes recipe for a different flavor idea.
WHY YOU WILL LOVE THIS RECIPE
You will love these Pineapple Upside Down Cupcakes because they are quick and friendly to make. The flavor is bright and light. The pineapple adds natural juice and a bit of tang. The brown sugar adds a caramel note that matches pineapple well. You do not need fancy tools or hard skills. Kids can help place the pineapple and cherries. These cupcakes also travel well. If you want other festive cupcake ideas for holidays, try this fun festive Christmas tree cupcakes for a seasonal treat.
HOW TO MAKE Pineapple Upside Down Cupcakes
This section tells you how to make the cupcakes step by step. The method is simple. You make a batter, place pineapple at the bottom of the liners, add batter, and bake. Use room temperature butter so it creams easily with the sugars. Drain the crushed pineapple well so the cupcakes do not get too soggy. You can add a cherry on each pineapple piece before you bake for a classic look. For other easy and fun cupcake methods, you might also like this festive reindeer cupcakes which show how small touches can make cupcakes special.
EQUIPMENT NEEDED
- Standard 12-cup cupcake pan
- Cupcake liners
- Mixing bowls (one large, one medium)
- Electric mixer or hand whisk
- Measuring cups and spoons
- Spatula or wooden spoon
- Cooling rack
- Toothpick or cake tester
Ingredients You’ll Need :
1 cup all-purpose flour, 1/2 cup brown sugar, 1/2 cup granulated sugar, 1/4 cup unsalted butter, softened, 1/2 cup milk, 1 teaspoon baking powder, 1/2 teaspoon vanilla extract, 1/2 cup crushed pineapple, drained, Maraschino cherries (optional for topping)
STEP-BY-STEP INSTRUCTIONS :
- Preheat the oven to 350°F (175°C) and line a cupcake pan with liners.
- In a mixing bowl, cream the softened butter and sugars until light and fluffy.
- Add the milk and vanilla extract, mixing until well combined.
- In another bowl, whisk together the flour and baking powder. Gradually add the dry ingredients to the wet ingredients, mixing until just combined.
- Place a spoonful of crushed pineapple at the bottom of each cupcake liner. Optionally, add a cherry on top of the pineapple.
- Pour the cupcake batter over the pineapple layer, filling each liner about two-thirds full.
- Bake for 20-25 minutes or until a toothpick inserted comes out clean.
- Let cool before serving. Enjoy your delicious Pineapple Upside Down Cupcakes!
HOW TO SERVE Pineapple Upside Down Cupcakes
Serve the cupcakes warm or at room temperature. If you want a glossy top, you can brush a small spoon of melted butter and brown sugar over each pineapple piece after they cool a bit, then flip the cupcakes out of the pan. These cupcakes look nice on a simple plate or on a tiered stand. For a party, arrange them in a circle and place a small mint leaf or extra cherry on top for color. If you want to pair with other themed cupcakes, you might add a small tray of spooky sweets such as those in the vampire bite Halloween cupcakes set to make a mixed dessert platter.
STORAGE & FREEZING : Pineapple Upside Down Cupcakes
Store these cupcakes in an airtight container at room temperature for 1-2 days. If your kitchen is warm, keep them in the fridge for up to 4 days. To freeze, place cupcakes in a single layer on a baking sheet and freeze until firm, about 1 hour. Then wrap each cupcake in plastic wrap and place them in a freezer bag or container. Freeze for up to 2 months. Thaw in the fridge overnight or on the counter for an hour before serving. Reheat in a low oven (about 300°F / 150°C) for 5-7 minutes if you want them warm.
SERVING SUGGESTIONS
- Serve with a scoop of vanilla ice cream for a classic combo.
- Top with a small spoon of whipped cream and a mint leaf.
- Pair with a cup of black tea or mild coffee for an afternoon treat.
- For brunch, place a few on a fruit platter with sliced mango and berries.
- Dust lightly with powdered sugar for a simple finish.
VARIATIONS
- Coconut Pineapple: Fold 1/4 cup shredded coconut into the batter for a tropical twist.
- Rum Flavored: Add 1 teaspoon of dark rum or rum extract to the batter for an island note.
- Spiced Version: Add 1/4 teaspoon ground cinnamon to the dry mix for a mild spice.
- Mini Cupcakes: Make mini versions by using a mini muffin tin and reduce bake time to 10-12 minutes.
- No-Cherry Option: Skip the maraschino cherry and use a thin pineapple slice or a small pineapple chunk for a cleaner look.
FAQs
Q: Can I use fresh pineapple instead of crushed pineapple?
A: Yes. Chop fresh pineapple small and drain any extra juice. Fresh pineapple gives a brighter taste but can make the cupcake slightly more moist, so drain well.
Q: Can I make this recipe gluten-free?
A: Yes. Replace the all-purpose flour with a 1-to-1 gluten-free flour mix. The texture may shift a bit, but it will still taste nice.
Q: Do I need to use maraschino cherries?
A: No. Cherries are optional. They add color and a sweet touch but do not change the core flavor.
Q: How do I stop the pineapple from making the cupcakes soggy?
A: Drain the crushed pineapple very well. You can press it in a sieve with a spoon to remove extra juice. Do not add the juice to the batter.
Q: Can I double the recipe?
A: Yes. Use two pans and bake in batches. The bake time stays the same for each pan.
MAKE-AHEAD TIPS FOR Pineapple Upside Down Cupcakes
You can make the batter in advance and store it in the fridge for up to 24 hours. If you want to prep the pineapple topping, place the pierced pineapple and cherry pieces into liners and cover the pan in plastic wrap. Keep in the fridge for up to a day and bake when ready. For larger events, bake the cupcakes a day ahead, cool them fully, and store in an airtight container in the fridge. Bring them to room temperature before serving, or warm briefly in the oven. For more ideas on prepping cupcakes ahead, check a similar quick idea in the apple cupcakes recipe which shows how to plan steps ahead for ease.

Pineapple Upside Down Cupcakes
Ingredients
Method
- Preheat the oven to 350°F (175°C) and line a cupcake pan with liners.
- In a mixing bowl, cream the softened butter and sugars until light and fluffy.
- Add the milk and vanilla extract, mixing until well combined.
- In another bowl, whisk together the flour and baking powder. Gradually add the dry ingredients to the wet ingredients, mixing until just combined.
- Place a spoonful of crushed pineapple at the bottom of each cupcake liner. Optionally, add a cherry on top of the pineapple.
- Pour the cupcake batter over the pineapple layer, filling each liner about two-thirds full.
- Bake for 20-25 minutes or until a toothpick inserted comes out clean.
- Let cool before serving.

