
Check out these cute little pineapple upside-down cheesecakes - they mix smooth cheesecake with a fun tropical twist. Each serving has a creamy cheesecake bottom topped with sweet caramelized pineapple, giving you an amazing mix of tastes and textures.
I came up with this after tons of kitchen experiments trying to get just the right mix of sweet, tangy, and tropical flavors in every mouthful.
Essential Ingredients
- Cream Cheese: Use the full-fat kind at room temp for the creamiest results
- Graham Crackers: Crush them yourself for the best crust feel and taste
- Pineapple: You can use fresh or canned, but make sure it's super dry
- Caramel: Grab a good one from the store or make your own

Cooking Steps
- Crust Making:
- Grind up those graham crackers real fine. Mix with melted butter until it sticks together when you squeeze it. Press it down hard into paper-lined muffin tins with the back of a spoon.
- Filling Creation:
- Whip the soft cream cheese until it's fluffy. Slowly add sugar while mixing. Drop in eggs one by one. Stir in vanilla just until mixed.
- Putting It Together:
- Fill each cup about three-quarters full. Tap the pan to get air bubbles out. Put pineapple pieces on top, pushing them down a bit. Bake until the sides are set but the middle still wobbles slightly.
The small size works way better than making one big cheesecake - they cook more evenly and you don't need to slice them up.
Cooling Instructions
Avoid those annoying cracks by cooling them slowly - just leave them in the oven with the door cracked open for about 10 minutes after turning it off.
Fruit Suggestions
Try to cut your pineapple chunks all the same size - about half an inch works great for cooking evenly and looking 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
You can switch things up with whatever fruit is in season - try fresh mango chunks or some caramelized peach slices.
These little treats show how you can take old-school desserts and turn them into fancy individual portions that'll impress everyone at your next gathering.

Frequently Asked Questions
- → Why should cream cheese and eggs be at room temperature?
- Room temperature ingredients blend smoothly, keeping the batter silky without lumps.
- → How do you avoid cracks in the cheesecakes?
- Don’t overmix, and bake with steam, like using a water bath, to stop cracking.
- → How long do these need to chill?
- Let the cheesecakes cool in the fridge for at least 4 hours, or even better, overnight.
- → Why does the pineapple need to be drained?
- Too much juice can mess up the cheesecake's texture, so make sure it’s drained and patted dry.
- → Are these good to make ahead?
- Yes! You can store them in the fridge and just add the caramel right before serving.