
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 a pinch of granulated sugar.
Mix graham cracker crumbs and melted butter until combined; press about 1 tablespoon of the mixture firmly into each liner on top of the pineapple.
Beat cream cheese and sugar together until smooth. Add eggs one at a time, mixing gently. Stir in vanilla.
Divide cheesecake batter evenly among muffin cups. 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.