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Mini Pineapple Upside-Down Cheesecakes

These Mini Pineapple Upside-Down Cheesecakes are individual treats featuring caramelized pineapple rings, juicy cherries, creamy cheesecake filling, and a soft spiced cake base. Perfect for parties, holidays, or whenever you want a tropical bite-sized dessert.
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Prep Time 25 minutes
Cook Time 25 minutes
Total Time 50 minutes
Servings: 12
Course: Dessert
Cuisine: American
Calories: 310
Ingredients Method Notes

Ingredients
  

  • For the Cake:
  • 4 large eggs at room temperature
  • 1 ¼ cups granulated sugar
  • ¼ cup dark brown sugar packed
  • ½ cup pineapple juice
  • 2 tsp rum or pure vanilla extract
  • 1 ½ cups all-purpose flour
  • 2 ¼ tsp baking powder
  • ½ tsp cinnamon
  • ¼ tsp salt
  • 2 tbsp cornstarch
  • For the Topping:
  • 6 tbsp unsalted butter
  • 1 ½ cups dark brown sugar packed
  • 1 tsp rum or vanilla extract
  • ⅛ tsp salt
  • 12 pineapple rings
  • 12 maraschino cherries

Method
 

  1. Prepare the Oven & Pan
  2. Preheat oven to 350°F (175°C). Grease a standard 12-cup muffin tin well, ensuring all edges are coated.
  3. Make the Caramel Topping
  4. In a saucepan over medium heat, melt the butter. Stir in brown sugar, rum (or vanilla), and salt. Cook until the sugar is dissolved and the mixture is glossy, about 2–3 minutes.
  5. Spoon about 2 tablespoons of the caramel mixture into each muffin cup.
  6. Add Pineapple & Cherries
  7. Place a pineapple ring into each muffin cup over the caramel. If needed, trim pineapple slices to fit.
  8. Place a maraschino cherry in the center of each ring.
  9. Prepare the Cake Batter
  10. In a mixing bowl, beat eggs with granulated sugar and brown sugar until thick and pale.
  11. Add pineapple juice and rum (or vanilla) and mix until combined.
  12. In another bowl, whisk flour, baking powder, cinnamon, salt, and cornstarch.
  13. Gradually fold dry ingredients into wet until just combined.
  14. Assemble & Bake
  15. Spoon the cake batter evenly over the pineapple-cherry layer in each muffin cup, filling almost to the top.
  16. Bake for 20–25 minutes, or until a toothpick comes out clean.
  17. Cool & Invert
  18. Let the cakes cool in the pan for 10 minutes.
  19. Run a knife around the edges, then carefully invert the muffin tin onto a baking sheet or platter. The caramel topping will drizzle down the sides.
  20. Serve & Enjoy
  21. Let cool slightly, then serve warm or at room temperature.

Notes

  • Use canned pineapple rings for consistent size and texture.
  • Muffin liners aren’t recommended—greasing the pan works best.
  • Inverting while warm is key—if the caramel sets too much, it can stick.