
These mini Pineapple Upside-Down Cheesecakes turn an old favorite into single-serving bites of tropical heaven. They bring together the smooth creaminess of cheesecake with the sweet caramel notes of pineapple upside-down cake, all sitting on a buttery graham base.
I took these tiny cheesecakes to our family gathering last summer and they were gone in moments. Everyone from the picky eaters to the dessert traditionalists couldn't get enough of the familiar tastes with an unexpected twist.
Quality Ingredients Matter
- Regular cream cheese blocks: They give you that rich, true cheesecake feel. Skip the tubs and go for solid blocks for best results
- Room temp eggs: When they're not cold, they mix in better and help create that velvety texture we all want
- Crushed graham crackers: Make sure they're ground really fine so your crust stays together nicely
- Real vanilla extract: It makes everything taste better. The real stuff costs more but adds much better flavor than the fake kind
- Drained pineapple pieces: Get rid of all extra juice by patting them dry so they don't make your cheesecake soggy
- Plain butter: Using unsalted lets you decide how the final dessert will taste, especially for the sweet topping
Making Your Dessert
- Start With The Base:
- Turn crackers into fine powder, then mix with melted butter until it looks like damp sand. Push down firmly in paper-lined muffin cups to form a solid bottom.
- Prepare Your Batter:
- Whip softened cream cheese until completely smooth. Slowly add sugar until it dissolves. Drop in eggs one by one, stirring gently just to combine. Carefully stir in vanilla.
- Build Each Treat:
- Pour creamy mixture over each base, filling cups about 75% full. Top with pineapple bits, pushing them slightly into the batter.
- Cook Them Right:
- Bake in hot oven until the sides are firm but middles still wobble slightly. Let them cool slowly to avoid cracks, then chill until fully set.
- Finish Them Off:
- Before serving, pour warm caramel over each mini cheesecake, letting it flow nicely down the sides.

My grandma always told me the key to amazing cheesecake was taking your time, and she wasn't wrong. Don't rush warming up your ingredients or cooling down your cheesecakes - it really does make all the difference in how they turn out.
Delicious Serving Suggestions
Make your dessert extra special by offering these mini treats alongside sticks of fresh tropical fruit. Add a little scoop of coconut sorbet for fancy flair, and serve with Kona coffee to balance the sweetness. For parties, try adding a splash of pineapple rum or some toasted coconut on top.
Fun Ways To Switch It Up
Try changing these treats by using other tropical fruits like mango or passion fruit for something different. You could swap out graham crackers for crushed coconut cookies to boost the tropical theme. If you want something lighter, try using Greek yogurt cream cheese - it's a bit tangier and has fewer calories but still keeps that great texture.
Storage And Enjoyment
Keep your mini cheesecakes in a sealed container in the fridge for up to five days. When you're ready to eat one, let it sit out for about 15 minutes to get that perfect creamy bite. Add the caramel just before eating for best results. If you want to freeze them, wrap each one in plastic and foil, then thaw overnight in your fridge.

I've spent years getting this recipe just right in my kitchen, and I've found these mini cheesecakes don't just taste good - they help create memories. Every time I make them, I think about happy family times and how they make people smile. Mixing tropical pineapple with classic cheesecake shows that sometimes the best treats come from playing around with old favorites.
Frequently Asked Questions
- → Can I prepare them in advance?
- Absolutely. Make them up to 48 hours earlier, chill them covered, and drizzle caramel right before serving.
- → Why are there cracks on my cheesecakes?
- Cracks happen if you overmix the batter or bake too hot. Mix less and use a water bath to avoid this.
- → Is fresh pineapple okay to use?
- Yes! Cut and dry it well to avoid extra juice, keeping the cheesecakes intact.
- → How do I know when they're ready?
- When edges look set and the middle jiggles slightly, they’re done. Cooling will firm them up.
- → Can I freeze these?
- Yes, store them frozen for 3 months. Wrap each one and thaw overnight in the fridge.