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

Add ½ teaspoon caramel sauce to each cupcake liner, place one pineapple chunk on top, and sprinkle with sugar.

Mix graham cracker crumbs and melted butter until combined, then press mixture into each liner on top of pineapple.

Beat cream cheese and sugar until smooth. Add eggs one at a time, mixing gently. Stir in vanilla extract.

Divide batter among muffin cups, filling nearly to top. Bake for 18-22 minutes until set but slightly jiggly. Cool for 15-20 minutes, then refrigerate for at least 2 hours.

Carefully remove liners and place cheesecakes upside down on plates. Garnish if desired.