Preheat the oven to 325°F (163°C). Line a 12-cup muffin pan with cupcake liners.

Add ½ teaspoon caramel sauce into each cupcake liner. Place one pineapple chunk over the caramel and sprinkle lightly with sugar.

In a medium bowl, combine graham cracker crumbs and melted butter until evenly mixed.

Press about 1 tablespoon of crust mixture into each liner on top of the pineapple layer.

In a large bowl, beat cream cheese and sugar until smooth and creamy, about 2–3 minutes.

Add eggs one at a time, mixing gently after each addition. Stir in vanilla extract.

Divide the batter evenly among the muffin cups, filling nearly to the top.

Bake the Mini Pineapple Upside Down Cheesecakes for 18–22 minutes, until the centers are mostly set with a slight jiggle.

Let the cheesecakes cool in the pan for 15–20 minutes.

Refrigerate for at least 2 hours before serving.

Carefully peel away cupcake liners and invert cheesecakes onto serving plates so the pineapple topping faces upward.

Garnish with whipped cream, cherries, or toasted coconut if desired.