1. Prepare the Caramelized Pineapple Topping:

• Melt the Butter: In a medium-sized saucepan or microwave-safe bowl, melt the 1/4 cup of unsalted butter. If using a microwave, melt in 30-second intervals, stirring in between, until fully melted.
• Add Brown Sugar: Stir in the 1/2 cup of packed light brown sugar into the melted butter until well combined and smooth. This mixture will form the caramel base for your topping.
• Prepare the Muffin Tin: Grease a 12-cup muffin tin generously with cooking spray or butter. This will prevent the cheesecakes from sticking and make removal easy.
• Assemble the Topping: Spoon about 1 tablespoon of the brown sugar mixture into the bottom of each muffin cup. Place a pineapple slice in the center of each cup, on top of the brown sugar mixture. If using maraschino cherries, place a cherry half in the center of each pineapple slice.
• Set Aside: Set the prepared muffin tin aside while you prepare the crust and filling.

2. Make the Graham Cracker Crust:

• Combine Dry Ingredients: In a medium bowl, combine the 1 1/2 cups of graham cracker crumbs and 1/4 cup of granulated sugar. Whisk together to ensure the sugar is evenly distributed.
• Add Melted Butter: Pour the 6 tablespoons of melted unsalted butter over the graham cracker crumb mixture.
• Mix Well: Stir with a fork until the mixture is evenly moistened and resembles damp sand. It should hold its shape when pressed together.
• Press into Muffin Cups: Spoon about 2 tablespoons of the graham cracker crust mixture into each muffin cup, on top of the pineapple topping. Use the bottom of a glass or your fingers to firmly press the crust evenly into the bottom of each cup, creating a compact base.

3. Prepare the Creamy Cheesecake Filling:

• Preheat Oven and Prepare Water Bath: Preheat your oven to 325°F (160°C). Place a large roasting pan on the bottom rack of the oven. Bring a kettle of water to a boil.
• Beat Cream Cheese and Sugar: In a large bowl, using an electric mixer (handheld or stand mixer), beat the softened cream cheese and 3/4 cup of granulated sugar until smooth and creamy. Scrape down the sides of the bowl as needed to ensure everything is well incorporated.
• Incorporate Eggs: Beat in the eggs one at a time, mixing until just combined after each addition. Be careful not to overmix at this stage, as overmixing can lead to cracks in the cheesecake.
• Add Sour Cream, Vanilla, and Salt: Stir in the 1/4 cup of sour cream, 1 teaspoon of vanilla extract, and a pinch of salt. Mix until just combined and the batter is smooth and homogenous.

4. Assemble and Bake the Mini Cheesecakes:

• Pour Filling into Muffin Cups: Spoon the cheesecake filling evenly over the graham cracker crust in each muffin cup, filling them almost to the top.
• Water Bath Baking: Carefully pour the boiling water into the roasting pan on the bottom rack of the oven, creating a water bath that should come about halfway up the sides of the muffin tin. The water bath helps to bake the cheesecakes gently and evenly, preventing cracking and ensuring a creamy texture.
• Bake: Bake for 25-30 minutes, or until the cheesecakes are set around the edges and slightly jiggly in the center. They should not be browned.
• Cool in Oven: Turn off the oven and leave the oven door slightly ajar. Let the cheesecakes cool in the oven for 30 minutes. This gradual cooling process further prevents cracking.
• Chill in Refrigerator: Remove the muffin tin from the water bath and let the cheesecakes cool completely at room temperature. Then, cover the muffin tin with plastic wrap and refrigerate for at least 4 hours, or preferably overnight, to allow the cheesecakes to fully set and chill.

5. Invert and Serve:

• Loosen Edges: Once the cheesecakes are thoroughly chilled, gently run a thin knife or spatula around the edges of each cheesecake to loosen them from the muffin cups.
• Invert onto Serving Plate: Place a serving plate or platter over the muffin tin and carefully invert the tin to release the mini cheesecakes. The caramelized pineapple topping should now be on top.
• Garnish (Optional): If desired, garnish with extra maraschino cherries, whipped cream, or a dusting of graham cracker crumbs.
• Serve and Enjoy! These Mini Pineapple Upside-Down Cheesecakes are best served chilled.