Quick & Easy Pineapple Upside Down Cupcakes

These QUICK & EASY Pineapple Upside Down Cupcakes are so simple but taste from-scratch and super amazing! I cannot even begin to tell you how EASY these Pineapple Upside Down Cupcakes are. Like, they’re basically foolproof.

And that’s saying something for a dessert that you’re required to flip upside down.

Growing up, we never had pineapple upside down cake. In fact, it wasn’t even on my radar until I was a teenager, and even then I believe I thought Sandra Lee invented it because I saw it on her cooking show that I was weirdly obsessed with. (Your teenage years are very, very odd time).

But little did I realize that my angel in white, Sandra Lee, did not invent the pineapple upside down cake. In fact, I’m not sure who invented it, but that person’s a genius and I want to buy them a pina colada because this is like, my newest favorite thing.

A couple weeks ago I made these Pineapple Upside Down Cheesecake Bars which were phenomenal. Creamy, dreamy and packed with pineapple flavor. What’s not to love? Since then, I’ve been dreaming of this fantabulous cake and all the different ways I could take those same flavors and incorporate them into a different dessert mashup. But then it hit me.

I didn’t even have a pineapple upside down cake on my blog.

Just go ahead and mail me the ‘worst food blogger ever’ award. Thanks.

I knew this had to change at once, 1) because I’ve been craving pineapple upside down cake fortnightly since I made my cheesecake bars, and 2) because I have yet to meet a person who isn’t mesmerized by the combination of bruleed pineapple and cake. I mean, it’s practically wizardry.

So here you go, in all its (SO SIMPLE OMG) glory: Pineapple Upside Down Cupcakes. Just like the cake, but in two-bite morsels that bake up perfectly, take hardly any effort, and are as gorgeous as they are tasty.

You start with a cake mix – duh. I mean sure, you could make your own scratch-made yellow cake – I’m not one to judge – but I like cake mix because I also like shortcuts. You don’t judge me, I don’t judge you. Capiche?

Flavor it up with the usual suspects: eggs, oil, and the juice from the pineapple you’re using. This adds a nice hint of pineapple to the cake batter without it being super pineapple-y. You can, of course, use the Pineapple cake mix if you can find it for a stronger flavor.

Then before you pour the batter into your muffin cups, you gotta make your brown sugar sawce. Mix melted butter and brown sugar. Ta-da! You are now a saucy genius. Distribute this mixture into greased (!!) muffin cups. Then add in your pineapple chunks (I used 3 per cup) and pour over your batter.

Now here’s where we can debate a little bit: some people like using crushed pineapple because they think there’s more pineapple per surface area and other reasons I’m sure. This is totally cool. I consulted with the pineapple upside down gods and they were like, “for sure dude, that rocks.” So it’s honestly to your preference whether or not you want to use crushed pineapple, pineapple chunks, pineapple tidbits… and whatever other shape they make pineapple in.

And then there’s the cherry debate. Do you bake the cherry in the cake mixture or top off the finished product? For these, I topped the finished product with the cherry so it’d look prettier in photos, and also because I couldn’t fit the plump maraschino cherry in between three pineapple chunks. So it was actually a matter of spacial problems than anything else. Again – do what feels right in your soul. Connect on a deeper level with the cherry. What does it tell you to do? Kumbaya, etc. etc.

And then bake it! It’s really that easy. Once it’s baked, let it set for a few minutes – sing your favorite song, fold a couple articles of clothing, walk your dog – and then very carefully flip it onto a baking sheet, tray, platter, etc. You may need to run a knife around the edge of the cake to help release it, but it’ll come out if you greased the daylights out of it… which you should always do.

Last part: EAT.

Now who wants to make me some?

These QUICK & EASY Pineapple Upside Down Cupcakes are so simple but taste from-scratch and super amazing!

Quick & Easy Pineapple Upside Down Cupcakes
Recipe type: Cakes/Cupcakes
Prep time: 
Cook time: 
Total time: 
Serves: 24
These Pineapple Upside Down Cupcakes are SO SIMPLE to make and they taste from-scratch and absolutely heavenly! No one will know they started with a box mix!
  • 1 box yellow cake mix
  • 3 eggs
  • ½ cup oil
  • 1 & ¼ cups pineapple juice (reserved from the can - if you cannot extract this much pineapple juice, get as much as you can and add water to make it to 1 & ¼ cups)
  • 1 large can pineapple chunks
  • ⅓ cup melted butter
  • ⅔ cup brown sugar
  • Maraschino cherries
  1. Preheat oven to 350 degrees F. Liberally grease 24 muffin cups with cooking spray. In a small bowl, whisk together the melted butter and brown sugar until combined. Drop heaping Tablespoonfuls of this brown sugar mixture into the bottoms of the cups. Place three pineapple chunks in a star pattern into the brown sugar mixture.
  2. In a large bowl, beat together the cake mix, eggs, oil and pineapple juice until combined, about 2 minutes. Portion the batter evenly among the muffin cups, filling about ¾ full.
  3. Bake for approx. 18-20 minutes or until a toothpick inserted near the center comes out clean. Cool in the pans for about 5-7 minutes, then very carefully invert onto a baking sheet, serving platter, tray, etc. You may need to run your knife along the edges of the cupcakes before releasing them.
  4. Garnish with cherries and serve warm or room temperature.

These QUICK & EASY Pineapple Upside Down Cupcakes are so simple but taste from-scratch and super amazing! Buttery, brown sugar-y, and with that bruleed pineapple flavor, these cupcakes are rock star! No wonder they’re a classic!

These QUICK & EASY Pineapple Upside Down Cupcakes are so simple but taste from-scratch and super amazing! Have a super sweet day!

xo, Hayley

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