These Mini Pineapple Upside-Down Cheesecakes bring back the sweetest memories of my grandmother’s kitchen, where I first learned to bake. I’ve combined two of my absolute favorite desserts the retro charm of pineapple upside-down cake and the creamy decadence of cheesecake into adorable single-serving treats that never fail to make people smile.

The moment you flip these little beauties over and see that perfect pineapple ring crowned with a maraschino cherry, you know you’re in for something special.

What are Mini Pineapple Upside-Down Cheesecakes?

Picture the most adorable mashup of two beloved desserts: the classic pineapple upside-down cake meets creamy cheesecake in perfect individual portions.

Each mini cheesecake starts with a caramelized brown sugar and butter base, topped with a ring of pineapple and a cherry center. Then comes the magic a velvety vanilla cheesecake batter poured over top. Once baked and flipped, you get these stunning little desserts with a self-saucing caramel topping that makes everyone go “wow!”

These mini cheesecakes give you all the nostalgia of a traditional pineapple upside-down cake but in a perfectly portioned size that’s ideal for parties, potlucks, or whenever you need a little something sweet. Plus, they’re easier to serve than a full-sized cheesecake, and everyone gets their own special presentation.

Ingredients

For the Topping (which goes on the bottom):

6 tablespoons unsalted butter, melted
3/4 cup brown sugar, packed
12 pineapple rings (from a 20 oz can), patted dry
12 maraschino cherries, stems removed
1/4 teaspoon vanilla extract
Pinch of sea salt

For the Cheesecake:

24 oz cream cheese, softened to room temperature
3/4 cup granulated sugar
3 large eggs, room temperature
1/4 cup sour cream
2 teaspoons vanilla extract
1/4 cup pineapple juice (reserved from the can)
2 tablespoons all-purpose flour
1/4 teaspoon salt

Recommended Equipment

Here’s what I keep handy when making these little beauties:

12-cup muffin tin (standard size)
Stand mixer or hand mixer
Mixing bowls (various sizes)
Measuring cups and spoons
Spatula and whisk
Parchment paper circles (optional but helpful)
Cookie scoop or ice cream scoop
Cooling rack
Paper towels (for drying pineapple rings)
Non-stick cooking spray

Instructions

Let me walk you through my tried-and-true process for creating these delightful mini cheesecakes:

First things first, I preheat my oven to 325°F (165°C). This slightly lower temperature helps prevent the cheesecakes from cracking and ensures even baking.
I start with the topping (which actually goes on the bottom). In a bowl, I mix the melted butter with brown sugar, vanilla extract, and that pinch of salt until it looks like wet sand. This mixture gets divided equally among my well-greased muffin cups.
Next comes my favorite part placing a pineapple ring in each cup. I make sure to pat them dry first (this helps prevent the caramel from becoming too runny). Then, I nestle a maraschino cherry in the center of each ring. This creates that classic upside-down cake look we all love.
For the cheesecake batter, I start by beating my room-temperature cream cheese until it’s super smooth. This usually takes about 2-3 minutes, and I always scrape down the sides of the bowl to catch any lumps.
I add the sugar and beat until the mixture looks light and fluffy about another 2 minutes. Room temperature ingredients are crucial here for achieving that perfect smooth texture.
One at a time, I add the eggs, mixing on low speed just until each one disappears into the batter. Over-mixing at this stage can lead to cracks, so I keep it gentle.
Next, in go the sour cream, vanilla extract, and pineapple juice. These ingredients add moisture and a hint of tropical flavor that complements the pineapple topping perfectly.
Finally, I fold in the flour and salt until just combined. The flour helps stabilize the cheesecake and prevent cracks.
I carefully spoon or scoop the batter over my prepared pineapple rings, filling each cup almost to the top. A cookie scoop makes this job much easier and neater.
These little treasures bake for about 22-25 minutes. I know they’re done when the edges are set but the centers still have a slight jiggle like Jell-O.
After cooling for about 30 minutes at room temperature, I run a knife around the edges and carefully flip them onto a serving plate. This is the moment of truth when that beautiful pineapple design is revealed!

Variations And Substitutions

Over time, I’ve experimented with several delicious variations:

Tropical Paradise Version:
I sometimes add 1/2 cup toasted coconut to the cheesecake batter and use coconut extract instead of vanilla. This gives the cheesecakes a piña colada twist that’s perfect for summer parties.

Lighter Option:
For a lighter version, I’ve successfully used Neufchâtel cheese instead of full-fat cream cheese and Greek yogurt in place of sour cream. The texture is slightly different but still delicious.

Mixed Fruit Version:
While pineapple is classic, I’ve tried this recipe with other fruits like peach slices or mandarin oranges. Each brings its own unique charm to the dessert.

Gluten-Free Adaptation:
I simply swap the all-purpose flour for a gluten-free blend, and my gluten-sensitive friends can enjoy these treats too!

How To Storage

Storage is key to maintaining the perfect texture and flavor of these mini cheesecakes:

In the refrigerator, they’ll stay fresh for up to 5 days when stored in an airtight container. I like to place them in a single layer to preserve the pretty topping.

For longer storage, these cheesecakes freeze beautifully for up to 2 months. I wrap each one individually in plastic wrap, then place them in a freezer-safe container. When I’m ready to serve, I thaw them overnight in the refrigerator.

The caramel topping might get a bit sticky after storage. I’ve found that letting them come to room temperature for about 30 minutes before serving helps restore that perfect texture.

Tips for Perfect Mini Pineapple Upside-Down Cheesecakes

Through plenty of trial and error, I’ve discovered some game-changing tips:

Temperature matters more than you might think. Room temperature ingredients blend more smoothly and create a silkier cheesecake texture. I set my ingredients out at least 2 hours before baking.

Don’t skip drying the pineapple rings! Extra moisture can make the caramel sauce too thin. I pat each ring thoroughly with paper towels before placing them in the muffin tin.

A water bath isn’t necessary for these mini versions, but placing a pan of hot water on the bottom rack of the oven while baking creates a humid environment that helps prevent cracks.

The cheesecakes will puff up while baking and sink a bit as they cool this is completely normal! The slight depression actually helps hold the caramel topping once they’re flipped.

Common Questions

1. Why did my caramel topping stick to the pan?

The first time this happened to me, I learned that greasing the pan thoroughly is crucial. Now I use non-stick spray and sometimes even parchment circles. If sticking occurs, warming the bottom of the pan slightly helps release the caramel.

2. Can I make these ahead for a party?

Absolutely! I often make them a day or two ahead. They actually taste better after the flavors have had time to meld in the refrigerator.

3. My cheesecakes cracked. What went wrong?

Usually, this happens from overmixing the batter or baking at too high a temperature. I always mix just until ingredients are combined and make sure my oven temperature is accurate with an oven thermometer.

4. Can I use fresh pineapple instead of canned?

While fresh pineapple is wonderful, I stick to canned for this recipe. The rings are perfectly sized and have a consistent moisture content that works best for the caramel topping.

Serving Suggestions

These mini cheesecakes are stunning on their own, but I love to dress them up sometimes! A dollop of whipped cream, a sprinkle of toasted coconut, or even a drizzle of caramel sauce takes them to the next level. For parties, I arrange them on a tiered cake stand with fresh mint leaves for a beautiful presentation that always gets compliments.

Creating these Mini Pineapple Upside-Down Cheesecakes has become one of my favorite baking adventures. They’re the perfect blend of nostalgic comfort and elegant presentation, making them ideal for any occasion, from casual family dinners to fancy dinner parties.