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Mini Pineapple Upside-Down Cheesecake Cake

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These adorable single-serve desserts layer caramel-glazed pineapple and cherry beneath a swirled cheesecake-and-vanilla-cake batter, delivering the nostalgia of pineapple upside-down cake with the creaminess of cheesecake in every mini bite.

Ingredients

Scale
  • 6 Tbsp (85 g) unsalted butter, melted and divided
  • 3/4 cup (150 g) packed light brown sugar
  • 12 canned pineapple rings, drained and patted dry
  • 12 maraschino cherries, drained
  • 8 oz (225 g) full-fat cream cheese, softened
  • 1/4 cup (50 g) granulated sugar, plus 1/4 cup (50 g) for cake batter
  • 2 Tbsp (30 g) sour cream
  • 2 large eggs, divided
  • 2 tsp pure vanilla extract, divided
  • 3/4 cup (95 g) all-purpose flour
  • 1/2 tsp baking powder
  • 1/4 tsp fine sea salt
  • 2 Tbsp (30 g) unsalted butter, melted (additional)
  • 1/4 cup (60 ml) whole milk

Instructions

  1. Preheat oven to 350 °F (175 °C). Lightly grease a 12-cup standard muffin pan.
  2. Spoon 1 tsp melted butter into each cup, sprinkle 1 Tbsp brown sugar over the butter, then press a pineapple ring (trim to fit) into each well. Nestle a cherry in the center of each ring; set pan aside.
  3. Cheesecake batter: In a medium bowl beat cream cheese until smooth. Add 1/4 cup granulated sugar, sour cream, 1 egg, and 1 tsp vanilla; beat until silky. Set aside.
  4. Cake batter: In another bowl whisk flour, baking powder, and salt. In a small bowl whisk remaining 1/4 cup granulated sugar, remaining egg, remaining 1 tsp vanilla, 2 Tbsp melted butter, and milk. Pour wet mixture into dry and stir just until combined.
  5. Divide cheesecake batter evenly over the prepared pineapple bases (about 1½ Tbsp per cup). Top with about 1½ Tbsp cake batter, smoothing lightly.
  6. Bake 22–25 minutes, or until tops are golden and a tester inserted into cake portion comes out clean.
  7. Cool in pan 10 minutes, then run a thin knife around edges and swiftly invert pan onto a platter. Lift pan to release mini cakes; spoon any caramel left in cups over tops.
  8. Serve warm or chilled. Refrigerate leftovers in an airtight container up to 3 days.

Notes

  • Blot pineapple rings well to avoid excess moisture that can inhibit caramelization.
  • For extra flavor, add 1 Tbsp dark rum to the butter-sugar mixture.
  • Cakes taste best the day they’re baked but set nicely after a night in the fridge.
  • Freeze (well-wrapped) up to 1 month; thaw overnight in the refrigerator.

Nutrition

Keywords: mini pineapple upside-down cheesecake, single-serve dessert, pineapple cheesecake cupcakes

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