
These pineapple upside down cupcakes are a tried-and-true crowd pleaser. Perfect for potlucks and gatherings, each cupcake delivers an individual serving of caramelized pineapple atop tender cake - no slicing or serving hassles required. The single-portion format ensures everyone gets that perfect ratio of sticky-sweet fruit topping and moist cake beneath.
This recipe consistently impresses even the most discerning dessert critics. The classic combination of caramelized pineapple, maraschino cherries, and buttery cake has a nostalgic appeal that makes these cupcakes a hit at any gathering.
Key Ingredients
- Canned pineapple rings: These provide consistent size and sweetness, perfect for individual cupcakes.
- Dark brown sugar: Creates a rich caramel topping with deep molasses notes.
- Unsalted butter: Essential for proper caramel texture and rich cake flavor.
- Maraschino cherries: Adds classic color contrast and traditional garnish.
- Vegetable oil: Keeps the cake extra moist and tender.

Step-by-Step Instructions
- Prepare the topping
- Combine melted butter and brown sugar until sandy in texture. Distribute mixture evenly in muffin cups, spreading with the back of a spoon.
- Arrange fruit
- Place one pineapple ring in each cup over sugar mixture. Center a dried maraschino cherry in each ring.
- Make the batter
- Thoroughly cream butter and sugar until light and airy. Incorporate eggs individually, then add vanilla extract.
- Combine ingredients
- Alternate adding dry ingredients and milk, beginning and ending with flour mixture. Gently fold in oil last.
- Fill cups
- Carefully spoon batter over pineapple to 3/4 full, avoiding disruption of fruit arrangement.
- Invert and unmold
- After baking, rest for exactly 5 minutes. Invert pan onto cooling rack in one swift motion.
This recipe transforms the classic pineapple upside down cake into perfectly portioned cupcakes. The tradition of caramelized pineapple desserts continues with this modern adaptation that makes sharing and serving a breeze.
Serving Suggestions
These cupcakes shine on their own, but pair beautifully with lightly sweetened whipped cream or a small scoop of vanilla ice cream. The contrast between warm cake and cold toppings creates an elevated dessert experience.
Variations
The recipe adapts well to modifications. Consider adding dark rum to the caramel for depth, or substitute peach slices and cinnamon for the pineapple. Mini versions using pineapple tidbits work for bite-sized treats.
Storage
Best served day-of, but keep loosely covered at room temperature for up to two days. Avoid tight sealing to maintain caramel texture. A brief warming refreshes texture. Not recommended for freezing.

Expert Tips
Use a thin knife around edges before inverting. Choose wider muffin tins for better pineapple presentation. Brush cakes with reserved pineapple juice after turning for extra moisture.
This recipe bridges classic dessert tradition with modern convenience. The individual portions offer consistent quality and easy serving, while maintaining the beloved flavors of traditional pineapple upside down cake. The combination of caramelized fruit and tender cake makes these cupcakes an enduring favorite for any occasion.
Recipe FAQs
- → Can I replace the canned pineapple with fresh ones?
- Using fresh pineapple isn’t ideal—it’s hard to get the same thickness and sweetness as canned rings. Canned works best!
- → What’s the best way to store these pineapple cupcakes?
- You can store them in a sealed container for up to two days at room temperature, or keep them in the fridge for up to five days. Let them come back to room temperature before eating.
- → How can I stop my cupcakes from sticking to the pan?
- Turn them out while warm. If they’re stuck, run a knife along the sides and gently tap the pan’s bottom to free them.
- → Is it possible to skip the cherries?
- Sure! Leave the cherries out or try other fruits like raspberries or blueberries—it’s all up to you.
- → Can I add extra spices to the recipe?
- Definitely! A bit of cinnamon, nutmeg, or even ginger would taste amazing alongside the pineapple flavor.