Step 1: Prep Your Tools and Ingredients

1. Preheat your oven to 325°F (163°C). Line a 12-cup muffin tin with liners or lightly grease it.

Step 2: Make the Pineapple Topping

1. Melt butter in a saucepan over medium heat. Stir in brown sugar until dissolved and bubbling.
2. Place 1 tablespoon of the caramel mixture into each muffin cup. Add a pineapple chunk or half a slice, and a maraschino cherry in the center.

Step 3: Prepare the Graham Cracker Crust

1. Mix crushed graham crackers, sugar, and melted butter until it resembles wet sand.
2. Press 1–1½ tablespoons of the mixture into each muffin tin on top of the pineapple topping.

Step 4: Make the Cheesecake Filling

1. Beat cream cheese and sugar until smooth.
2. Add eggs one at a time, then mix in vanilla extract and sour cream until combined.

Step 5: Assemble and Bake

1. Spoon cheesecake filling over the crust, filling each cup almost to the top. Smooth with the back of a spoon.
2. Bake for 20–25 minutes, until edges are set but centers jiggle slightly.
3. Cool in the pan for 10 minutes, then refrigerate for at least 2 hours.

Step 6: Flip and Serve

1. Carefully run a knife around each cheesecake. Invert onto a plate to reveal the pineapple topping.