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I can't wait for you to try my go-to Pineapple Upside-Down Cupcakes! These little bites of joy glow with sticky caramel, juicy pineapple, and cheery cherries sitting on the softest, fluffiest cake. They always spark big grins and remind me of island getaways. Seriously, they brighten up any gathering.
Irresistible Tropical Delight
The best thing about these cupcakes is that the brown sugar darkens and gets syrupy, mixing right into the pineapple to make this shiny, sweet top. That pop of pineapple flavor goes all through the treat, thanks to juice mixed right into the cake. And you've gotta love those ruby cherries making everything look extra fun.
What to Grab
- Topping Stuff:
- Super soft butter, melted, for sticky sweetness
- A handful of brown sugar that turns super glossy
- Cut pineapple circles trimmed to fit your pans
- Cherry-red maraschino cherries for some pizzazz
- Cake Mix-ins:
- Eggs for fruity richness
- White and brown sugars together for a deeper taste
- Whole milk for soft cupcakes
- Room-temp butter for easy mixing
- Pineapple juice for max tropical taste
- Real vanilla extract
- All-the-time basics: flour, salt, baking soda, and baking powder
Time to Bake
- Baking Prep:
- Crank up your oven to 350°F and grease your cupcake pans—don't be shy with that butter.
- Topping Time:
- Start with mixing melted butter and brown sugar. Drop a scoop into each slot, then slide in pineapple and pop in a cherry.
- Put Together the Batter:
- Whip up your sugars with butter until it looks like clouds, blend in eggs and vanilla, and switch back and forth adding dries and juicy stuff.
- Bake and Wait:
- Scoop the batter over those fruity layers and bake till the tops look golden and you smell sweetness, about 20-25 minutes.
- Flip & Reveal:
- Give 'em a quick 5-minute rest, then tip the whole pan upside down onto your favorite dish. Ready for wow moments.
Dig In
They're my favorite straight-from-the-oven when the caramel is lemon drop gooey. They'll be fine for a couple days, though to be honest, they vanish almost immediately at my place.
Top Tricks
Load up on the butter when greasing the tins or they'll stick—no one wants that mess. Fresh pineapple is awesome if you'd rather skip canned stuff. PRO TIP: Splash in some rum for a big flavor boost.
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Fast Facts
- Fresh or Canned? Go for either, but cut fresh super thin for the best fit.
- Plan Ahead: They're great made the night before.
- Serving Win: Hot out of the oven or cooled off, they're crowd-pleasers.
- Flipping Success: Act fast—you want a confident flip for a perfect top.
Common Questions
- → How come the topping clung to the pan?
Try greasing your pan generously and flip them out while they're still a bit warm. If you wait until they cool, they'll stick more.
- → Could I swap canned pineapple for fresh?
Canned fruit's just more reliable for these since fresh pineapple tends to leak extra juice and isn't as sweet.
- → Any tips to stop batter from overflowing?
Don’t go past about 3/4 full because it’ll puff as it bakes. Setting the pan on a baking sheet isn’t a bad idea either, just in case.
- → Is it okay to bake these in advance?
They’re best if you eat them the same day, but you can stash them in a sealed container for up to two days. Just know the topping may lose some of its caramel vibe.
- → What made my fruit float to the top?
Really press those pineapple and cherries into the butter-sugar mix before you add cake batter. Also, don’t stuff too much in each cup.