
Mini pineapple upside-down cakes capture all the classic flavors of the beloved dessert in perfect individual portions. Each cake features a ring of caramelized pineapple topped with a bright maraschino cherry, sitting atop a tender vanilla cake. The single servings ensure every bite has the ideal balance of sticky-sweet fruit topping and moist, fluffy cake underneath.
These mini cakes are a tried-and-true crowd pleaser at any gathering. The aroma of caramelizing butter and brown sugar draws everyone to the kitchen, while the individual portions make serving effortless. They work equally well for casual family dinners or elegant dinner parties.
Essential Ingredients
- All-purpose flour: Creates ideal cake structure and texture
- Cornstarch: Ensures tender, delicate crumb
- Dark brown sugar: Provides rich caramel flavor
- Pineapple rings: Fresh or canned work well
- Maraschino cherries: Adds classic garnish
- Vanilla extract: Enhances flavor depth
- Pineapple juice: Infuses tropical taste throughout
Baking Instructions
- Preparation:
- Position rack in center and heat oven to 350°F
- Pan Setup:
- Thoroughly butter jumbo muffin tin
- Topping Base:
- Mix melted butter and brown sugar, divide between cups
- Fruit Layer:
- Center pineapple rings in cups, add cherries
- Make Batter:
- Cream butter until light, about 3 minutes
- Combine Wet Ingredients:
- Add eggs one at a time, mixing well
- Finish Batter:
- Alternate dry ingredients and juice in three parts

Years of baking experience have proven that room temperature ingredients truly make a difference. They blend more smoothly and create a more even, tender cake texture.
Serving Suggestions
Serve slightly warm with vanilla ice cream for an elevated dessert. Pair with spiced coffee for brunch. Create an impressive display using cake stands at varying heights. Finish with rum caramel sauce or fresh whipped cream.
Recipe Variations
Try seasonal fruits like peaches in summer or apples in fall. Add cardamom or ginger for unique flavor. Use gluten-free flour blend if needed. Top with chopped macadamia nuts for crunch.
Storage Tips
Keep in airtight container with wax paper between layers. Best within 2 days at room temperature or 5 days refrigerated. Reheat wrapped in foil at 300°F for 10 minutes or microwave 20 seconds.

This perfected recipe combines nostalgic appeal with modern convenience. The caramelized pineapple topping and tender cake create an irresistible classic dessert that consistently impresses guests while being surprisingly simple to prepare.
Frequently Asked Questions
- → Can I make these without rum?
- Of course! Just use vanilla extract instead of rum in both parts of the recipe.
- → Why is cornstarch added to the cake batter?
- It makes the cake softer and improves the texture.
- → Is it okay to use a standard-size muffin tray?
- Yes, but the baking time will need to be adjusted since smaller tins cook faster.
- → Why should I wait 5 minutes before flipping the cakes?
- This lets the caramel set slightly, while it’s still warm enough not to stick.
- → Can these be prepared ahead of time?
- They’re best fresh, but if needed, you can refrigerate them for up to 3 days.