
These bite-sized pineapple upside-down cheesecakes are total tropical bliss - think of your beloved creamy cheesecake but in cute individual servings, each crowned with sweet caramelized pineapple that brings that traditional upside-down cake vibe. After tweaking this creation through countless tasty trials, I've nailed the sweet spot between velvety cheesecake and zesty island flavors.
I took these to a family dinner last week, and even my picky aunt who guards her classic cheesecake recipe like gold wanted to know how I made them. That's when I knew I'd hit on something really good!
Key Ingredients
- Cream Cheese: Go for full-fat at room temp for extra smoothness. I've learned that using it cold just gives you lumps in your mix
- Graham Crackers: Newly crushed ones create the tastiest base. I crush mine in the blender for just the right feel
- Pineapple: Fresh or canned works fine, but make sure you drain it well and pat it dry so your treats don't turn mushy
- Caramel Sauce: Making your own is awesome, but grabbing a nice one from the store does the trick too

Step-by-Step Guide
- Base Building:
- Blitz graham crackers until they're super fine. Stir in melted butter until it looks like damp sand. Pack firmly into your cupcake liners using a spoon to push down hard. The tighter you pack it, the better your base will stay together.
- Mixing Your Filling:
- Whip cream cheese until it's perfectly smooth. Slowly add sugar while you keep mixing. Add eggs one by one, making sure to scrape the bowl often. Mix in vanilla just until everything's combined. You want your mix to be totally smooth.
- Putting It All Together:
- Pour filling into each liner about three-quarters full. Tap the pan lightly to get rid of air bubbles. Put pineapple bits on top and push them down slightly. Bake just until the sides set but the middle still wobbles a bit.
I first came up with these when I was trying to mash up two desserts I love. After a bunch of tries, I found out that making small ones actually works way better than one big cake.
Smart Cooling Method
The trick to avoiding cracks is changing the temperature slowly. I always let them sit in the turned-off oven with the door open a crack for about 10 minutes after baking.
Pineapple Cutting Tips
Getting all your pineapple pieces the same size means they'll cook evenly and look prettier when served. I try to cut mine into little half-inch squares.
Prep Them Early
They actually taste way better after sitting overnight! I make mine a day ahead and just add the caramel right before I serve them.
Try Other Fruits
While pineapple is the classic choice, I've had great luck using mango chunks and even sweet caramelized peaches during summertime.
Whenever I whip up these mini treats, I can't help thinking about how sometimes the tastiest recipes come from throwing together favorite desserts in fresh ways. They've become my go-to party sweet, mixing familiar comfort flavors with a surprising island twist.

Frequently Asked Questions
- → Why should eggs and cream cheese be soft?
- Softened cream cheese and eggs mix easily, giving you lump-free cheesecake batter.
- → How can I stop cracks from forming?
- Don't overmix the batter. Using steam in the oven also helps keep cracks away.
- → How much chilling time is needed?
- Pop them in the fridge for at least four hours, or overnight, to set perfectly.
- → Why drain the pineapple?
- Too much juice makes the cakes soggy, so get rid of all that extra liquid first.
- → Can I prep them in advance?
- Absolutely, they store in the fridge well. Just drizzle the caramel when serving.