
Mini pineapple upside down cheesecakes strike the perfect balance between creamy and bright. Each little cake offers layers of tangy cheesecake, buttery graham cracker crust, and a sweet caramelized pineapple topping crowned with a cherry. These minis are my favorite to bring to spring brunches because they never last more than a few minutes on the dessert table.
I first whipped these up for a family get-together and everyone insisted on taking extras home. Now they are a holiday staple I make for both kids and adults.
Ingredients
- Crushed graham crackers: This creates a sturdy, buttery base. Make sure the crumbs are fine for the best texture
- Sugar: Adds sweetness and helps the crust hold together. Look for white granulated sugar that pours easily
- Melted butter: Binds the crust and gives a rich flavor. Use real butter for best results
- Cream cheese: Provides the creamy tangy structure. Full-fat block cream cheese works best for the smoothest filling
- Sugar: Gives the cheesecake its signature sweetness. Use fresh sugar with no clumping
- Vanilla extract: Rounds out the flavor with warm notes. Pure extract makes a difference if you have it
- Large eggs: Bind the batter and help the cheesecakes rise. Bring to room temperature for easy blending
- Crushed pineapple: The star of the topping. Drain well and choose pineapple that smells sweet not fermented
- Brown sugar: Melts to create a caramel-like topping. Pack it tight so you get rich flavor in every bite
- Maraschino cherries: Add that iconic pop of color. Look for firm brightly colored cherries
Step-by-Step Instructions
- Make the Crust:
- Mix crushed graham crackers sugar and melted butter in a bowl until the mixture feels like wet sand. Firmly press it into the bottoms of each muffin cup so the layer is even and compact
- Prepare the Cheesecake Filling:
- Beat softened cream cheese sugar and vanilla together until completely smooth with no lumps. Add the eggs one by one mixing well between each so the batter stays airy. Gently fold in the drained crushed pineapple last so the filling is well distributed
- Assemble the Mini Cheesecakes:
- Spoon the cheesecake mixture over each crust dividing evenly. If needed smooth the tops with a small spatula so they bake evenly
- Add the Topping:
- Sprinkle brown sugar on the surface so each cake will caramelize on top while baking. Place a cherry right in the center of each one
- Bake and Cool:
- Place the muffin pan in a preheated 325 degree oven. Bake for about 20 to 25 minutes until the cheesecakes look set at the edges and just a little jiggle remains in the center. Let cool completely before trying to remove them for the cleanest results

One year we doubled the recipe for a summer BBQ and had none left by the end of the night. My niece loved helping press the crusts and always requests extra cherries on hers.
Storage Tips
Refrigerate the cheesecakes in an airtight container for up to four days. They also do well if you freeze them tightly wrapped for up to one month. Defrost overnight in the fridge and they honestly taste just as creamy as fresh.
Ingredient Substitutions
You can swap crushed vanilla wafers for graham crackers if preferred. Coconut or pecan pieces mixed into the crust is a tasty twist. Fresh pineapple chunks work as long as you finely chop and drain well. And if you want a lighter version try neufchatel cheese in place of some cream cheese.
Serving Suggestions
These look beautiful on a tiered dessert tray with extra cherries scattered around. It is fun to set out small bowls of whipped cream or a drizzle of caramel for guests to customize their own treats at parties. At home we sometimes add a sprinkle of toasted coconut before serving too.

Cultural and Historical Context
Pineapple upside down cakes have roots in American home baking dating back to when canned pineapple was first popularized in the early 1900s. Turning them into mini cheesecake cups is a modern twist that combines two beloved desserts and makes portioning a breeze.
Recipe FAQs
- → What type of pineapple works best for this dessert?
Both fresh and canned crushed pineapple work well. Make sure to drain thoroughly to avoid excess moisture.
- → How do you prevent the cheesecakes from sticking to the pan?
Use paper liners or lightly grease the muffin tin before adding the crust and filling to ensure easy release.
- → Can these be made ahead of time?
Yes, chill them after baking for several hours or overnight. This helps set the texture and makes serving easier.
- → What is the best way to serve these mini cheesecakes?
Serve chilled, optionally topped with whipped cream and extra cherries for a decorative touch.
- → How do I achieve a smooth cheesecake filling?
Start with softened cream cheese and beat until creamy before adding sugar, eggs, and other ingredients gradually.