Step 1: Prepare the Caramel Base

Preheat your oven to 350°F (175°C). Lightly grease an 8-cup muffin tin. This step is crucial to prevent the mini cheesecakes from sticking and ensures easy removal once baked. In a small, microwave-safe bowl, or in a saucepan over low heat, melt the butter. Be careful not to overheat or burn the butter; you just want it fully melted. Once melted, stir in the brown sugar until it’s completely combined with the butter and forms a smooth, slightly thick caramel mixture. Divide this caramel mixture evenly among the prepared muffin cups, placing about a teaspoon or slightly more in the bottom of each cup. This caramelized base will create that signature upside-down cake flavor and a beautiful, gooey topping for your cheesecakes.

Step 2: Arrange the Pineapple Topping

Now, for the fun part – creating the “upside-down” element! Take your drained pineapple slices and place one slice into each muffin cup, directly on top of the caramel layer. If your pineapple slices are large, you might need to cut them in half or quarters to fit neatly into the muffin cups. Next, take your halved maraschino cherries and place one or two halves (depending on size and preference) into the center of each pineapple ring. The cherries not only add a pop of color but also a burst of sweetness that complements the pineapple perfectly. Press them gently into the pineapple and caramel to ensure they are secure.

Step 3: Make the Cheesecake Filling

In a large mixing bowl, beat the softened cream cheese with an electric mixer until it is smooth and creamy. This is a key step for achieving a lump-free cheesecake filling. Ensure your cream cheese is truly at room temperature; this will make it much easier to beat and incorporate smoothly. Gradually add the granulated sugar to the cream cheese, continuing to beat until the mixture is light and fluffy. Scrape down the sides of the bowl as needed to ensure everything is evenly mixed.

Next, beat in the eggs one at a time, mixing well after each addition. Don’t overmix at this stage; just mix until each egg is fully incorporated. Overmixing can introduce too much air into the batter, which can lead to cracks in your cheesecakes during baking. Stir in the sour cream and vanilla extract. Mix until just combined and the batter is smooth and homogenous. Finally, gently fold in the all-purpose flour. Fold until just combined and no streaks of flour remain. Be careful not to overmix after adding the flour, as this can develop the gluten and make the cheesecake tougher.

Step 4: Prepare the Optional Graham Cracker Crust (If Using)

While the crust is optional, it adds a delightful textural contrast and a buttery, graham cracker flavor that enhances the overall cheesecake experience. If you’re choosing to make the crust, in a small bowl, combine the graham cracker crumbs, melted butter, and sugar. Mix well until the crumbs are evenly moistened and resemble wet sand. Press about a tablespoon of this mixture into the bottom of each muffin cup, on top of the pineapple and caramel layer. Use your fingers or the back of a spoon to gently press the crust evenly and firmly into each cup.

Step 5: Assemble and Bake the Mini Cheesecakes

Carefully spoon the cheesecake filling evenly over the pineapple topping (and crust, if using) in each muffin cup. Fill each cup almost to the top, leaving a little space as the cheesecakes will puff up slightly during baking. Smooth the tops of the cheesecakes with the back of a spoon or an offset spatula for a neat and even finish.

Place the muffin tin in the preheated oven and bake for 20-25 minutes, or until the cheesecakes are set around the edges but still slightly jiggly in the center. A slight jiggle in the center is desirable as the cheesecakes will continue to set as they cool. Do not overbake them, as this can make them dry and crumbly.

Step 6: Cool and Chill

Once baked, remove the muffin tin from the oven and let the mini cheesecakes cool in the tin for about 15-20 minutes at room temperature. This allows them to set further and prevents them from cracking due to sudden temperature changes. After the initial cooling period, carefully run a thin knife or spatula around the edges of each cheesecake to loosen them from the muffin cups. Invert a serving plate or cutting board over the muffin tin and quickly flip it over to release the cheesecakes. The caramel and pineapple topping should now be on top, beautifully showcasing the “upside-down” effect.

Transfer the cheesecakes to the refrigerator and chill for at least 2-3 hours, or preferably overnight. Chilling allows the cheesecakes to fully set and develop their flavor. They are best served cold, allowing the flavors to meld together and the texture to become perfectly creamy and firm.

Step 7: Serve and Enjoy!

Before serving, you can garnish the mini pineapple upside down cheesecakes with extra maraschino cherries, a drizzle of caramel sauce, or a dollop of whipped cream, if desired. These are delicious served on their own, but a little extra touch elevates them even further. Enjoy these delightful and perfectly portioned mini desserts!