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Mini Pineapple Upside-Down Cheesecakes

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Delight in these Mini Pineapple Upside-Down Cheesecakes — a perfect fusion of creamy cheesecake and sweet, caramelized pineapple topping. These bite-sized treats combine a buttery graham cracker crust with a rich cheesecake filling, finished with a golden pineapple slice and cherry on top. Ideal for parties, dessert tables, or anytime you crave a tropical twist on classic cheesecake!

Ingredients

  • 1 cup graham cracker crumbs
  • 3 tbsp unsalted butter, melted
  • 2 tbsp brown sugar
  • 8 oz cream cheese, softened
  • 1/4 cup granulated sugar
  • 1 large egg
  • 1/2 tsp vanilla extract
  • 1/4 cup sour cream
  • 6 pineapple rings (canned or fresh, cut into halves or quarters to fit)
  • 6 maraschino cherries
  • 1/4 cup brown sugar (for topping)
  • 2 tbsp unsalted butter (for topping)

Instructions

  • Preheat oven to 325°F (165°C).
  • In a small bowl, mix graham cracker crumbs, melted butter, and 2 tbsp brown sugar until combined. Press mixture evenly into the bottom of a greased muffin tin (one for each cheesecake).
  • In a saucepan, melt 2 tbsp butter with 1/4 cup brown sugar over medium heat, stirring until bubbly and caramelized. Spoon about 1 tsp of the caramelized mixture onto each crust. Place a piece of pineapple and a cherry on top of the caramel.
  • In a mixing bowl, beat the cream cheese and granulated sugar until smooth. Add egg, vanilla extract, and sour cream; mix until creamy and well combined.
  • Spoon the cheesecake batter over the pineapple layer, filling each cup about 3/4 full.
  • Bake for 18–22 minutes or until the center is set but still slightly jiggly.
  • Cool in the pan for 10 minutes, then run a knife around edges and invert onto a cooling rack or plate to reveal the pineapple topping. Refrigerate for at least 2 hours before serving.

Notes

  • For a gluten-free option, use gluten-free graham crackers or almond flour crust.
  • Use fresh pineapple rings for a fresher taste, but canned works perfectly too.
  • Let cheesecakes chill fully for the best texture and flavor.
  • You can substitute cherries with pineapple chunks or skip them entirely.