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Mini Pineapple Upside-Down Cheesecakes

Mini Pineapple Upside-Down Cheesecakes


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  • Author: Olivia Harper
  • Total Time: 40–45 minutes
  • Yield: 12 mini cheesecakes 1x
  • Diet: Vegetarian

Ingredients

Scale

For the Topping (which goes on the bottom):

  • 6 tablespoons unsalted butter, melted
  • 3/4 cup brown sugar, packed
  • 12 pineapple rings (from a 20 oz can), patted dry
  • 12 maraschino cherries, stems removed
  • 1/4 teaspoon vanilla extract
  • Pinch of sea salt

For the Cheesecake:

  • 24 oz cream cheese, softened to room temperature
  • 3/4 cup granulated sugar
  • 3 large eggs, room temperature
  • 1/4 cup sour cream
  • 2 teaspoons vanilla extract
  • 1/4 cup pineapple juice (reserved from the can)
  • 2 tablespoons all-purpose flour
  • 1/4 teaspoon salt

Instructions

  1. First things first, I preheat my oven to 325°F (165°C). This slightly lower temperature helps prevent the cheesecakes from cracking and ensures even baking.
  2. I start with the topping (which actually goes on the bottom). In a bowl, I mix the melted butter with brown sugar, vanilla extract, and that pinch of salt until it looks like wet sand. This mixture gets divided equally among my well-greased muffin cups.
  3. Next comes my favorite part placing a pineapple ring in each cup. I make sure to pat them dry first (this helps prevent the caramel from becoming too runny). Then, I nestle a maraschino cherry in the center of each ring. This creates that classic upside-down cake look we all love.
  4. For the cheesecake batter, I start by beating my room-temperature cream cheese until it’s super smooth. This usually takes about 2-3 minutes, and I always scrape down the sides of the bowl to catch any lumps.
  5. I add the sugar and beat until the mixture looks light and fluffy about another 2 minutes. Room temperature ingredients are crucial here for achieving that perfect smooth texture.
  6. One at a time, I add the eggs, mixing on low speed just until each one disappears into the batter. Over-mixing at this stage can lead to cracks, so I keep it gentle.
  7. Next, in go the sour cream, vanilla extract, and pineapple juice. These ingredients add moisture and a hint of tropical flavor that complements the pineapple topping perfectly.
  8. Finally, I fold in the flour and salt until just combined. The flour helps stabilize the cheesecake and prevent cracks.
  9. I carefully spoon or scoop the batter over my prepared pineapple rings, filling each cup almost to the top. A cookie scoop makes this job much easier and neater.
  10. These little treasures bake for about 22-25 minutes. I know they’re done when the edges are set but the centers still have a slight jiggle like Jell-O.
  11. After cooling for about 30 minutes at room temperature, I run a knife around the edges and carefully flip them onto a serving plate. This is the moment of truth when that beautiful pineapple design is revealed!

Notes

  • Temperature matters more than you might think. Room temperature ingredients blend more smoothly and create a silkier cheesecake texture. I set my ingredients out at least 2 hours before baking.
  • Don’t skip drying the pineapple rings! Extra moisture can make the caramel sauce too thin. I pat each ring thoroughly with paper towels before placing them in the muffin tin.
  • A water bath isn’t necessary for these mini versions, but placing a pan of hot water on the bottom rack of the oven while baking creates a humid environment that helps prevent cracks.
  • The cheesecakes will puff up while baking and sink a bit as they cool this is completely normal! The slight depression actually helps hold the caramel topping once they’re flipped.
  • Prep Time: 20 minutes
  • Cook Time: 20–25 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 1 Mini Cheesecake
  • Calories: 250-280 kcal
  • Sugar: 22-26g
  • Sodium: 150-200mg
  • Fat: 14-18g
  • Saturated Fat: 7-10g
  • Unsaturated Fat: 4-6g
  • Trans Fat: 0-0.5g
  • Carbohydrates: 28-32g
  • Fiber: 0-1g
  • Protein: 3-5g
  • Cholesterol: 40-60mg