Mini Pineapple Upside Down Cheesecake

Craving a dessert that’s cute, creamy, and has a tropical twist? These mini pineapple upside down cheesecakes are exactly what your dessert table needs. They’re the perfect marriage between the classic pineapple upside down cake and a rich, velvety cheesecake—made in personal-sized portions that are as fun to look at as they are to eat. Whether you’re hosting a summer gathering or just want to treat yourself to something special, these little guys are a total crowd-pleaser.

Picture this: a buttery brown sugar and pineapple layer baked right into the bottom (or technically, the top!) of a rich cheesecake, topped off with a bright maraschino cherry. Then imagine all that flavor packed into a cupcake-sized treat. It’s one of those recipes that looks fancy, but is surprisingly easy to make at home. Plus, they bake faster than a full cheesecake and chill quicker, too, which means dessert is on the table a whole lot sooner.

The first time I made these, I was experimenting with ways to reinvent a summer favorite. I wanted something light, fruity, and creamy—but still indulgent. Cheesecake and pineapple just made sense. After a few test batches (read: delicious failures), I landed on this version. They’re now one of my go-to desserts for potlucks, birthdays, and weekend cravings. Everyone loves them—even the folks who claim they’re “not cheesecake people.”

What I really enjoy about this recipe is how versatile it is. You can swap in crushed pineapple or pineapple rings, add a splash of rum for a pina colada vibe, or even try it with other fruits like peaches. But trust me, the classic pineapple and cherry combo never disappoints.

Why You’ll Love It

• Perfectly Portioned – These mini cheesecakes are individually sized, making them ideal for parties, gatherings, or late-night sweet cravings without overindulging.
• Tropical Flavor in Every Bite – The combination of caramelized pineapple, a pop of cherry, and rich cheesecake is a tropical dream come true.
• No Water Bath Needed – Unlike traditional cheesecake, these minis are baked without fuss—no water bath, no cracks, no stress.
• Make-Ahead Friendly – You can easily bake them a day or two in advance and store them chilled. They only get better with time!
• Beautiful Presentation – That golden pineapple slice and bright cherry on top make them look bakery-worthy with minimal effort.

Ingredient List

For the Topping:

• ¼ cup unsalted butter, melted
• ½ cup light brown sugar, packed
• 6 pineapple rings, cut to fit muffin cups
• 6 maraschino cherries

For the Crust:

• ¾ cup graham cracker crumbs
• 2 tablespoons granulated sugar
• 3 tablespoons unsalted butter, melted

For the Cheesecake Filling:

• 12 oz cream cheese, softened
• ⅓ cup granulated sugar
• 1 teaspoon vanilla extract
• 1 large egg
• 2 tablespoons sour cream
• 1 tablespoon all-purpose flour

Ingredient Notes

• Pineapple rings – I like to use canned pineapple rings in juice (not syrup)—they’re soft, sweet, and easy to cut to size.
• Maraschino cherries – Go for the bright red ones for that classic look! Just pat them dry a bit so they don’t bleed into the topping.
• Graham cracker crumbs – You can use store-bought crumbs or crush your own. A food processor makes this quick and easy.
• Cream cheese – Always use full-fat cream cheese for the creamiest texture. Let it soften at room temperature to avoid lumps.
• Sour cream – Adds a slight tang and creaminess that balances the sweetness of the topping.
• All-purpose flour – Just a little helps the cheesecake set up perfectly without being too dense.

Kitchen Equipment Needed

• 12-cup muffin pan – For baking the mini cheesecakes; I recommend a non-stick metal one for easy release.
• Mixing bowls – You’ll need a few for separating the crust, filling, and topping mixtures.
• Electric hand mixer or stand mixer – Helps blend the cream cheese until super smooth (I love using my hand mixer for smaller batches).
• Measuring cups and spoons – For accurate measurements—especially important with baking!
• Small saucepan or microwave-safe bowl – To melt butter and mix the brown sugar topping.
• Spoon or small spatula – Great for pressing the crust and spreading the filling evenly.
• Cooling rack – Allows your cheesecakes to cool down evenly before chilling.
• Knife or offset spatula – To gently loosen the cheesecakes from the pan after chilling.

Instructions

1. Preheat and Prep the Pan

• Preheat your oven to 325°F (163°C).
• Lightly grease a 12-cup muffin pan with non-stick spray or a bit of melted butter.
• Optional: place cupcake liners if you’d prefer an easier release, but these look best baked directly in the pan for that caramelized top.

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2. Make the Pineapple Topping

• In a small bowl, mix together ¼ cup melted butter and ½ cup brown sugar until combined.
• Spoon about 1 tablespoon of the mixture into the bottom of each muffin cup.
• Cut your pineapple rings to fit neatly into the muffin wells and press one piece into the sugar mixture in each cup.
• Place a maraschino cherry in the center of each pineapple piece.

Pro Tip: Pat the pineapple and cherries dry with a paper towel before placing them in the pan to avoid excess moisture, which can prevent proper caramelization.

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3. Make the Graham Cracker Crust

• In a bowl, combine ¾ cup graham cracker crumbs, 2 tablespoons sugar, and 3 tablespoons melted butter.
• Stir until the texture resembles wet sand.
• Add about 1 tablespoon of crust mixture on top of each pineapple layer and press down gently using the back of a spoon or your fingers to compact it.

Pro Tip: A small flat-bottomed glass or spice jar works wonders for evenly pressing the crust.

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4. Make the Cheesecake Filling

• In a medium bowl, beat 12 oz softened cream cheese until smooth and fluffy—about 1 minute.
• Add ⅓ cup sugar and mix until fully incorporated.
• Mix in 1 teaspoon vanilla extract, 2 tablespoons sour cream, and 1 tablespoon flour until smooth.
• Crack in the egg and beat on low speed just until blended. Avoid overmixing.

Pro Tip: Overmixing can introduce air bubbles and cause the cheesecake to puff too much or crack—gentle mixing is key once the egg goes in.

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5. Fill and Bake

• Spoon the cheesecake filling evenly over the crusts—each cup should be about ¾ full.
• Smooth the tops with a spoon or mini spatula.
• Bake for 18–22 minutes, or until the centers are set and only slightly jiggly in the middle.

Pro Tip: If the edges look set and the center wiggles slightly when gently shaken, they’re ready. Don’t wait for them to brown!

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6. Cool and Chill

• Let the cheesecakes cool in the pan for about 30 minutes.
• Carefully run a thin knife or offset spatula around the edges to loosen them.
• Refrigerate in the pan for at least 2 hours, or until fully chilled and firm.
• Once chilled, gently pop each cheesecake out onto a plate—pineapple side up!

Pro Tip: If they’re stubborn, briefly dip the bottom of the pan in warm water to loosen the caramel base.

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Ready to serve? These beauties shine all on their own, but a dollop of whipped cream never hurts!

Tips and Tricks for Success

• Use room temperature ingredients – Especially the cream cheese and egg. It makes mixing smoother and prevents lumps in the batter.
• Dry the fruit – Pat the pineapple slices and cherries dry before assembling to keep the topping from getting watery.
• Don’t overbake – The cheesecakes should still have a little jiggle in the center when they come out. They’ll firm up as they chill.
• Chill thoroughly – Let them set for at least 2 hours in the fridge. The flavor improves and the texture becomes beautifully creamy.
• Loosen carefully – Run a thin knife around the edge before removing to keep the pineapple layer intact and gorgeous.

Ingredient Substitutions and Variations

• Crust alternatives – Try crushed vanilla wafers, digestive biscuits, or even gingersnaps for a spiced twist.
• Fruit swaps – Replace pineapple with canned peach slices or mango for a different tropical flavor.
• Cherry-free option – Leave out the cherry or swap with a small strawberry slice or blueberry if you prefer.
• Gluten-free version – Use gluten-free graham crackers and a gluten-free flour blend.
• Dairy-free option – Sub in dairy-free cream cheese, sour cream, and butter. Taste may vary slightly but still delicious!
• Mini cheesecake bars – Make this recipe in a lined square pan and cut into bars instead of using a muffin tin.

Serving Suggestions

• Chilled with whipped cream – A swirl of whipped cream on top adds lightness and looks pretty for parties.
• With a drizzle of caramel or pineapple syrup – A little extra sweetness on top brings out the fruity flavor.
• On a dessert platter – Pair with mini chocolate cupcakes and fresh fruit for a stunning dessert spread.
• Topped with toasted coconut flakes – For a tropical crunch that complements the pineapple beautifully.
• My favorite way? Straight from the fridge, with a hot cup of coffee in the afternoon—sweet, cool, and totally satisfying.

Storage and Reheating Instructions

• Refrigerate in an airtight container for up to 4–5 days. Place a piece of parchment between layers if stacking.
• Freeze for longer storage – Wrap each mini cheesecake tightly in plastic wrap and foil, then freeze for up to 2 months.
• To thaw, place in the fridge overnight—don’t thaw at room temp to avoid sogginess.
• No reheating needed – These are meant to be enjoyed chilled, straight from the fridge or just slightly softened.
• Avoid microwaving – It can ruin the texture and melt the topping. Stick with a chilled or lightly room-temp serving.

Frequently Asked Questions

Can I make these ahead of time?

Yes! These mini cheesecakes are perfect for making ahead. You can bake them up to 2 days in advance and store them chilled until ready to serve. They actually taste even better the next day!

Can I use fresh pineapple instead of canned?

You can, but make sure it’s sliced thin and soft enough to caramelize. Canned pineapple is more consistent in size and texture, which helps with even baking.

How do I prevent the cheesecakes from sticking?

Make sure to grease your muffin tin well, and don’t skip running a knife around the edges after cooling. You can also use silicone muffin pans or liners for easier removal.

Can I make this recipe gluten-free?

Absolutely! Just use gluten-free graham crackers and swap the all-purpose flour for a gluten-free baking blend. Everything else stays the same.

What if I don’t have a muffin pan?

You can bake these in a mini cheesecake pan (with removable bottoms) or even turn it into a full 8-inch cheesecake—just adjust the baking time accordingly.

Can I double the recipe?

Yes! Just make sure you have two muffin pans ready to go. They’ll bake just the same, but you’ll want to rotate the pans halfway through for even baking.

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Did you try this recipe? Let me know in the comments how it turned out!

Don’t forget to share your photos on Instagram and tag me (@tasiahub_) or use the hashtag (#tasiahub). I’d love to see your creations!