Mini Pineapple Upside Down Cakes

What are these cute little things?

These are basically the adorable baby cousins of the classic pineapple upside down cake we all know and love. Instead of one big cake, you get individual mini cakes with those gorgeous caramelized pineapple rings on top (well, technically on the bottom when you’re baking them). They’ve got that perfect sticky-sweet caramel top, tender vanilla cake underneath, and the maraschino cherry center that makes everyone smile. Plus, they’re single-serving, so no awkward cutting and serving – just flip and enjoy!

Why You’ll Love This Recipe

Let me count the ways:

• These little guys are WAY cuter than a regular cake. Like, Instagram-worthy cute.
• Everyone gets their own perfect portion with the ideal ratio of caramelized pineapple to cake.
• No fighting over the corner pieces – every piece is equally awesome.
• They bake faster than a full cake, so you get to eat them sooner (always a win).
• You can make them in a muffin tin – no fancy equipment needed!
• They’re perfect for parties because they’re pre-portioned and easy to serve.
• That moment when you flip them over and reveal that perfect pineapple top? Pure kitchen magic.
• They freeze surprisingly well, so you can have pineapple upside down cake emergency rations.

The Good Stuff You’ll Need

For the Caramel Pineapple Topping:

• 1/2 cup (1 stick) unsalted butter (just use the real stuff, we’re not counting calories here)
• 1 cup brown sugar, packed (dark brown gives deeper flavor, but light works too)
• 1 can (20 oz) pineapple rings in juice (you’ll use the juice too, so don’t drain it!)
• 12 maraschino cherries (get the ones without stems to make your life easier)
• Optional but awesome: 2 tablespoons rum or 1 teaspoon rum extract

For the Cake:

• 1 1/2 cups all-purpose flour
• 1 1/2 teaspoons baking powder
• 1/4 teaspoon salt
• 1/2 cup unsalted butter, softened (yep, more butter – it’s worth it)
• 3/4 cup granulated sugar
• 2 large eggs, room temperature (cold eggs mess with the batter, trust me)
• 1 teaspoon vanilla extract (the real stuff, not the fake garbage)
• 1/4 cup milk
• 1/4 cup reserved pineapple juice (from that can you didn’t drain)

Equipment:

• 12-cup muffin tin (the standard size, not mini or jumbo)
• Nonstick spray or extra butter for greasing
• Knife or kitchen scissors for cutting pineapple rings
• Small saucepan for the caramel
• Electric mixer (stand or hand) for the cake batter
• Cooling rack

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Let’s Do This

Prep Work (10 minutes):

1. Preheat your oven to 350°F (175°C). This is not negotiable – your oven needs to be fully preheated for these to bake properly!
2. Grease the heck out of your muffin tin. Like, seriously, go to town with the butter or nonstick spray. These babies are sticky and you’ll thank me later when they pop right out.
3. Drain your can of pineapple rings, but SAVE THE JUICE in a bowl. You’ll need it for the cake batter.
4. Cut the pineapple rings: If you’re using standard muffin tins, you’ll need to cut the rings into smaller pieces. I usually cut each ring into quarters (so you get 4 triangle-ish pieces from each ring). If you found the mini pineapple rings, congrats, you can skip this step!

Make the Caramel Topping (10 minutes):

1. In a small saucepan, melt that stick of butter over medium-low heat. Don’t rush this by cranking the heat – burnt butter is sad butter.
2. Once melted, add the brown sugar and stir until it dissolves into the butter, about 2-3 minutes. If you’re using rum, add it now and let it bubble for another minute (the alcohol will cook off).
3. Remove from heat and let it cool slightly while you prep the fruit.

Assemble the Topping (5 minutes):

1. Spoon about 1 tablespoon of your caramel mixture into each muffin cup. It should cover the bottom nicely.
2. Arrange pineapple pieces in each cup, on top of the caramel. If you’re using the quartered rings, you can fit 3-4 pieces in each cup in a pretty pattern.
3. Place a maraschino cherry in the center of each cup. This is non-negotiable – it’s not a proper pineapple upside down cake without the cherry!

Make the Cake Batter (15 minutes):

1. In a medium bowl, whisk together the flour, baking powder, and salt. Set aside.
2. In a large bowl, beat the softened butter and granulated sugar with an electric mixer until light and fluffy, about 2-3 minutes. Don’t skimp on this time – you’re creating air pockets that make your cake fluffy!
3. Add eggs one at a time, beating well after each. Then beat in the vanilla extract.
4. Mix the milk and 1/4 cup of the reserved pineapple juice together in a measuring cup.
5. Gradually add the flour mixture to the butter mixture, alternating with the milk-pineapple mixture. Start and end with the flour (so it’s flour, liquid, flour, liquid, flour). Mix just until combined after each addition – don’t beat the daylights out of it or you’ll end up with tough cakes.

Bake Those Beauties (20-25 minutes):

1. Spoon the batter evenly over the pineapple and caramel in each muffin cup. Fill them about 3/4 full – the batter will rise!
2. Bake in your preheated oven for 20-25 minutes, until the tops are golden and a toothpick inserted in the center comes out clean.
3. Remove from the oven and let them cool in the pan for EXACTLY 5 minutes. Set a timer! Too short and they fall apart, too long and the caramel glues them to the pan permanently.

The Big Flip (The Moment of Truth):

1. After 5 minutes, place a large cutting board or baking sheet over the top of the muffin tin.
2. Holding the board firmly against the tin, flip everything over in one confident motion. No hesitating!
3. Let the tin sit upside down on the board for about 1 minute to let all the caramel drip down onto the cakes.
4. Carefully lift the tin off. If any pineapple pieces or cherries stick to the tin, just pop them back onto the cakes where they belong.
5. Let the cakes cool on the board for another 5-10 minutes before serving (if you can wait that long).

Serving Suggestions

• These mini cakes are absolutely perfect served warm with a scoop of vanilla ice cream that gets all melty on top.
• For brunch, serve with a dollop of Greek yogurt and call it “breakfast” (I won’t tell).
• If you’re feeling extra, drizzle with a bit more caramel sauce or a splash of rum.
• They’re amazing with coffee, especially a nice dark roast that cuts through the sweetness.
• For parties, arrange them on a platter with some fresh pineapple chunks and mint leaves for that “I definitely went to culinary school” look.

Switch It Up

Got the basics down? Try these twists:

• Tropical Paradise: Add 1/2 cup shredded coconut to the cake batter and use coconut milk instead of regular milk. Top with a sprinkle of toasted coconut after flipping.
• Boozy Version: Soak the cherries in rum overnight before using them. Your guests will get a tasty surprise!
• Mixed Fruit: Replace some pineapple pieces with other canned fruits like peaches or apricots. Just make sure to pat them dry first.
• Spice It Up: Add 1/2 teaspoon of cinnamon and a pinch of nutmeg to the cake batter for a warm, spiced version.
• Brown Butter Upgrade: Brown the butter before making the caramel for a nutty, complex flavor that’ll make people ask for your secret.
• Mini Bundt Version: If you have a mini bundt pan, these look SPECTACULAR made in those. Just adjust baking time (they might take a few minutes longer).

Make-Ahead and Storage Tips

• These little cakes are actually best served the day they’re made, but hey, real life happens.
• You can store leftovers in an airtight container at room temperature for 2 days. The caramel will continue to soak into the cake, making them super moist.
• For longer storage, refrigerate up to 5 days, but bring to room temperature or warm slightly before serving.
• They freeze surprisingly well! Wrap individually in plastic wrap, then foil, and freeze for up to 3 months. Thaw overnight in the fridge, then warm in the microwave for about 20-30 seconds.
• To reheat: A quick 15 seconds in the microwave makes them taste almost fresh-baked.

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Questions People Actually Ask

Q: Can I make these without maraschino cherries? My kid thinks they’re gross.
A: I mean, technically yes, but they’ll be missing that classic look. Try using fresh berries like raspberries or even small strawberry pieces instead.

Q: My caramel hardened before I could get it in the muffin tins! What did I do wrong?
A: You probably cooked it a bit too long. No worries – just warm it back up on low heat, stirring constantly, until it’s pourable again.

Q: Can I use fresh pineapple instead of canned?
A: You ambitious chef, you! Yes, but it’s trickier. Fresh pineapple doesn’t have that syrupy sweetness of canned, so you might want to sauté fresh pineapple pieces in a bit of butter and sugar first. Also, you’ll need to substitute the juice with pineapple juice from a bottle.

Q: Help! My cakes stuck to the pan and now I have a disaster!
A: First, breathe. Then, put the pan back in a warm oven (about 300°F) for 3-4 minutes to re-melt the caramel. Try the flip again and they should release. If all else fails, spoon everything into dessert glasses, layer with whipped cream, and call it “Pineapple Upside Down Trifle.” Fancy!

Q: Can I make this as one big cake instead?
A: Absolutely! Use a 9-inch cake pan and increase the baking time to about 35-40 minutes. The flip is trickier with a big cake though, so make sure your plate is bigger than your pan!

Q: I don’t have an electric mixer. Can I still make these?
A: Yes, you’ll just need some serious arm strength. Make sure your butter is REALLY soft, and use a wooden spoon to cream it with the sugar until it’s light and fluffy. It’ll take longer, but consider it your workout for the day.

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