
Check out these cute little pineapple upside-down cheesecakes - they mix smooth cheesecake with a tropical twist. Each serving has a silky cheesecake topped with sweet, caramelized pineapple that creates an amazing combo of tastes and textures.
We spent tons of time in the kitchen tweaking this recipe to get just the right mix of sweet, tangy and tropical in every mouthful.
Essential Components
- Cream Cheese: Use full-fat, room temperature for the creamiest results
- Graham Crackers: Crush them yourself for the best crust flavor
- Pineapple: Either fresh or canned works, just make sure it's super dry
- Caramel: Pick a good ready-made one or whip up your own

Cooking Instructions
- Crust Making:
- Turn graham crackers into fine crumbs. Mix with melted butter until it clumps when squeezed. Press firmly into muffin tin liners using a spoon.
- Filling Creation:
- Whip the soft cream cheese until it's fluffy. Slowly add sugar while mixing. Drop in eggs one by one. Mix in vanilla just until blended.
- Finishing Up:
- Pour batter into cups leaving room at top. Tap the pan to pop air bubbles. Add pineapple chunks on top, pushing them in slightly. Bake until edges are set but middle still wobbles a bit.
Making smaller cakes works better than one big one - they cook more evenly and are easier to serve.
Cooling Advice
Stop cracks from forming by cooling slowly - just leave them in the oven with the door cracked open for 10 minutes after baking.
Fruit Suggestions
Cut your pineapple into same-sized half-inch chunks so they cook evenly and look pretty.
Make-Ahead Options
Make them a day early so flavors can blend together. Wait to add the caramel until right before you serve them.
Other Topping Ideas
Try switching it up with fresh mangoes or brown sugar peaches instead.
These tiny treats show how you can turn old-fashioned desserts into fancy individual portions that'll impress at any party.

Frequently Asked Questions
- → Why does it matter if the ingredients are room temperature?
- It makes blending them smoother, leaving you with a lump-free batter.
- → How do I avoid cracks appearing?
- Stir just enough to combine and add steam with a water bath to prevent cracks.
- → How much time do they need in the fridge?
- Put them in the fridge for at least 4 hours, or overnight for the best taste.
- → Why do I need to dry the pineapple?
- Extra pineapple juice can mess up the texture, so pat it dry after draining.
- → Can I make them ahead of time?
- Definitely! Prep them early, refrigerate, and drizzle the caramel when serving.