
Check out these cute little pineapple upside-down cheesecakes - they mix smooth, rich cheesecake with a fun tropical twist. Each bite-sized treat has a creamy cheesecake topped with sweet, caramelized pineapple, giving you an amazing combo of tastes and textures.
We spent tons of time in the kitchen playing with this recipe until we got just the right mix of sweet, tangy and tropical in every mouthful.
Essential Components
- Cream Cheese: Go for full-fat and make sure it's soft to get that super smooth texture
- Graham Crackers: Crush them yourself for the best-tasting, perfect-textured crust
- Pineapple: You can use fresh or canned, just make sure you drain and pat it dry
- Caramel: Pick up a good one from the store or whip up your own

Cooking Steps
- Base Preparation:
- Turn graham crackers into fine crumbs. Mix with melted butter until it sticks when pressed. Press firmly into your lined muffin tin using a spoon.
- Cheesecake Mixture:
- Whip the soft cream cheese until it's fluffy. Slowly add sugar while mixing. Add eggs one by one. Mix in vanilla just until everything's combined.
- Final Steps:
- Fill each cup about three-quarters full. Tap the pan to get rid of air bubbles. Put pineapple pieces on top, pushing them in slightly. Bake until the edges are set but the middle's still a bit wiggly.
The small individual servings work way better than making one big cheesecake - they cook more evenly and they're easier to serve.
Cooling Instructions
To keep the tops from cracking, let them cool down slowly - just leave them in the oven with the door cracked open for about 10 minutes after baking.
Fruit Advice
Cut your pineapple into half-inch pieces that are all about the same size so they cook evenly and look pretty.
Make-Ahead Options
You can make these a day early and they'll taste even better. Just wait to add the caramel until right before you serve them.
Other Topping Ideas
Try switching it up with different fruits like fresh mango chunks or caramelized peach slices.
These little treats show how you can take old-school desserts and turn them into fancy individual portions that'll impress at any party.

Frequently Asked Questions
- → Why do the ingredients need to be at room temp?
- It makes the batter blend smoothly, so you don’t end up with any lumps.
- → How can I avoid cracks in the cheesecakes?
- Don’t mix the batter too much, and use a water bath in the oven for moist heat.
- → How long should they chill in the fridge?
- Let them cool for at least 4 hours, or overnight if you can wait!
- → Why is it necessary to drain the pineapple?
- Extra moisture can mess up the texture, so dry it well after draining.
- → Can I make them ahead of time?
- Definitely! Keep them cold in the fridge, and add the caramel drizzle right before serving.