This Pineapple Upside Down Cheesecake is a crave-worthy mix of two fantastic desserts: it combines a foundation of rich cheesecake with a topping of juicy baked pineapple covered in brown sugar; the result is a dish that blends the best of both worlds.

Have you ever tasted a cake made with pineapple flipped upside down? In that case, you are aware that the traditional recipe produces a very addicting sweet. It’s a vanilla cake with a light and airy sweetness that comes from the addition of pineapple juice, and it’s baked on top of a delicious layer of caramelized pineapple, butter, and brown sugar. When the cake is turned over onto a platter, the pineapple layer will be on the very top, where it will look beautiful and taste great. 

Now, in this recipe, we are going to take that same concept and apply it to cheesecake. The combination of pineapple and authentic cheesecake cooked from scratch is heavenly, particularly when accompanied by a crust made of buttery graham crackers, maraschino cherries, and the traditional topping made of brown sugar and butter.




  • 7 T spoons.Of butter – melted. 
  • ½ Cup.Of packed brown sugar. 
  • Canned pineapple – I used 10 slices. 
  • 13 Maraschino cherries. 
  • 1 Cup.Of graham cracker crumbs. 
  • 3 T spoons.Of white sugar. 
  • 3 T spoons.Of soft butter. 



  • Cream cheese; I used 24-oz at room temp.
  • 1 Cup.Of light brown sugar.
  • 3 T spoons.Of all-purpose flour.
  • ½ Cup.Of sour cream – at room temp.
  • 6 T spoons.Of pineapple juice. 
  • 2 t spoons.Of vanilla extract. 
  • 3 whole eggs– at room temp.


Step 1: Prepare the oven to 300 degrees Fahrenheit. Prepare a springform pan with a diameter of 9 inches by lining the bottom with parchment paper and greasing the edges.

Step 2: Mix together the brown sugar and the 4 tablespoons of melted butter. Spread this all over the bottom of the pan in an equal layer. 

Step 3: To prevent the pineapple slices from adding any additional moisture to the topping, pat them dry before using them. 

Step 4: Place the pineapple slices and cherries in a floral pattern on top of the brown sugar, then line the edges of the pan (see recipe post photos for guidance). 

Step 5: Mix together the graham cracker crumbs, the sugar, and the 3 tbsp of butter that are left over. Spread this on top of the pineapple slices in a uniform layer, and then gently push it into the slices to incorporate it.


Step 1: Beat the cream cheese, brown sugar, and flour together on low speed in a large bowl until they are smooth and well mixed.

Step 2: After that, stir the pineapple juice, sour cream, and vanilla extract into the mixture. Mix on low speed until everything is mixed well. 

Step 3: Add the eggs one at a time, mixing slowly to combine after each one. If you need to, scrape the sides of the bowl to make sure everything is mixed well. Then, fill the crust with the cheesecake batter. 

Step 4: Put the springform pan inside another pan that is bigger. Fill the outside pan with enough warm water to reach about halfway up the sides of the springform pan. If the water goes over the top edge of the foil, it could leak into the cheesecake. 

Step 5: The middle should be firm, but still move around. After turning off the oven, keep the door shut for the next half an hour. The cheesecake will keep cooking, but it will also start to slowly get cooler. The cheesecake will cool more slowly if you crack the oven door for 30 minutes. This keeps the cracks from happening. 

Step 6: Take the cheesecake out of the oven and the wrapping around the water bath. Put it in the fridge for 5 to 6 hours or overnight, until it is firm. 

Step 7: Take the cheesecake out of the springform pan and put it on a plate. Carefully flip the cheesecake by placing a serving tray on top of the cake (which will become the bottom of the cake). 

Step 8: Then, using a butter knife, pry the parchment paper off from the pan’s bottom. Keep the cheesecake in the fridge until it’s time to serve.