Pineapple Upside Down Cupcakes
Pineapple Upside Down Cupcakes – a mini version of your favorite cake with butter, brown sugar, pineapple, and a cherry on top!
These Pineapple Upside Down Cupcakes are good warm or at room temperature so they’re great for parties or luaus.
Pineapple Upside Down Cupcakes
In a perfect world, I would make these from scratch. And by all means if you want to, go right ahead.
But sometimes a doctored up cake mix does wonders. I mean adding brown sugar and butter to cake mix? Sounds like a sure win to me.
These Pineapple Upside Down Cupcakes have been calling to me for years. Try not to burn the top of your mouth off eating them straight out of the oven. I did.
WHAT ARE PINEAPPLE UPSIDE DOWN CUPCAKES?
Pineapple Upside Down Cupcakes are a mini version of your favorite cake with butter, brown sugar, pineapple, and a cherry on top!
- First, spoon some melted butter, crushed pineapple, brown sugar, and a cherry in the bottom of a muffin tin.
- Next, top with the cupcake batter and bake.
- Finally, invert the cupcakes for beautiful Pineapple Upside Down Cupcakes.
I always have plenty of helpers in the kitchen. My son poured a teaspoon (or two) of butter in each cupcake tin. Then he put a tablespoon of brown sugar on top.
Then he put a cherry right in the center of the brown sugar. 
I tried using crushed pineapple and pineapple tidbits to see which one worked better.The crushed pineapple won the experiment by a long shot.
It had way more flavor and looked prettier. The tidbits give a nice flower shape but most of them got stuck in the tin and the pineapple flavor wasn’t as strong.
The cupcake batter is just made according to the package directions but with replacing the water in the recipe with pineapple juice. Make sure you don’t over fill your tins.
Invert the cooked cupcakes onto waxed or parchment paper and you’re done!
If you enjoyed watching how to make pineapple upside down cupcakes, you’ll love these recipes:
Banana Coconut Upside Down Cake
Reese’s Peanut Butter Cupcakes
Pineapple Upside Down Cupcakes
Ingredients
- cooking spray
- 1/2 cup butter , melted
- 1 1/2 cups brown sugar
- 24 maraschino cherries
- 1 (20 ounce) can crushed pineapple (reserve juice)
- 1 (18.25 ounce) package yellow cake mix (and oil and eggs called for on the package)
- 1 1/3 cups pineapple juice (you just need as much pineapple juice as water called for on the cake mix package - see note)
- confectioners' sugar for dusting
Instructions
- Preheat oven to 350 degrees and spray 24 muffin cups with cooking spray.
- Line a work surface with parchment or waxed paper.
- Spoon 1 teaspoon melted butter into the bottom of each sprayed muffin cup.
- Spoon 1 tablespoon brown sugar in each muffin cup.
- Press a maraschino cherry into the center of the brown sugar in each muffin cup.
- Spoon a heaping tablespoon of crushed pineapple over the cherry and compact it with the back of a spoon into an even layer.
- Mix cake mix according to the package directions, replacing the water with pineapple juice. This may vary according to which cake mix you use. In large bowl with electric mixer on low speed until moistened, about 30 seconds. Turn mixer speed to medium and mix for 2 minutes.
- Pour pineapple cake batter into the muffin cups, filling them almost to the top.
- Bake in the preheated oven on the middle rack until a toothpick inserted into the center of a cupcake comes out clean, about 20 minutes.
- Allow cupcakes to cool at least 5 minutes before inverting muffin cups onto the waxed paper to release. Serve with pineapple and cherry sides up. Sprinkle cupcakes lightly with confectioners' sugar if desired.
Recipe Notes
Just replace the water called for in your cake mix with pineapple juice. You should be able to reserve the juice from the crushed pineapple and have enough pineapple juice to use here. If you are a little shy on the amount of juice, just use water to fill the rest of the liquid called for in the recipe.
*Some people like the look of pineapple tidbits better for this recipe. I tried both and the crushed pineapple has a lot more flavor and looked prettier.
Source: Allrecipes - http://allrecipes.com/recipe/pineapple-upside-down-cupcakes/detail.aspx?mxt=t06dda
I will be making these using a mini muffin pan, What is the baking time you used?
My 8 year old Granddaughter loves helping with this recipe. And her 6 year old brother helps
with the brown sugar. Therefore we end up with some what of a mess. But it’s all worth it to
do this with my Grandkids. Thank for the ideas.
Excellent recipe!! I did 2 things differently — I used jumbo muffin pans and pineapple rings. They came out like mini cakes! Everyone loved the look, the size and the taste. Thanks for a great recipe!
Good to know. Thank you!
Just made these and my husband has a new favorite dessert!! Any tips on storing until the next day?!
Hello, fellow blogger here. I am thinking about making these for a large church dinner. I’ll be using 24 ct muffin pans, so I wanted to ask how easily do these come out of the tins when you invert? Do they slip right out easily, cherry and all? Thanks
You need to really grease the tin and not cook too long or the brown sugar will carmelize and stick.
This was a great recipe. My daughter Nikkie and I
fallow step by step no problem. It was delicious we made over 60 cupcakes and a cake with the left over. (Riquisimo!!!) Delicious will post pictures
THanks Margie. Glad you liked it!
These are insanely good! I didn’t compact the pineapple mixture which may have helped them come out of the pan easier. It was a nonstick pan as well, so that probably helped. I went easier on the brown sugar, just a sprinkling in the bottom of each cup as well. They took about 16-17 minutes at 350 (just check for when the tops start to turn golden brown). Hoping the family will like them for xmas; if not, I’m fine with taking them back home!
Thanks for the tips!!
I had a 20 oz can of crushed pineapple and a standard jar of maraschino cherries. There was barely enough pineapple to make 12 cupcakes, and there were 16 cherries in the jar. Keep this in mind, since the cake mix makes 24 cupcakes.
I made 12 upside-down-cupcakes.
They were good, but ALL THE TOPPING STUCK TO THE SILICON PAN, even though I buttered it well. I just scraped it all back onto the cupcakes. It looks good — haven’t had a chance to try it yet!
Sorry you’re stuck! That’s strange. It slips right out for me.
I found your recipe and made these for the first time 2 years ago! I am back again to make them for what will be my 3rd time now. They have been a crowd pleaser and received a lot of compliments both times around. I used tidbits the first 2 times but I have crushed pineapple this time around and am excited to it out that way. Thanks for the yummy recipe!
I’m just wondering if anyone has tried this recipe using a pineapple cake mix?
Ooh I bet that would be amazing.
These are so delicious! I made them without the cherry but I wanted to eat a hundred of them when they came out of the oven.
It’s a magical combo.
I’m trying your pineapple upside down cupcakes recipe & adding a bit of pecan pieces to mine, ummm😋
I think that would be awesome!
Can you use cupcake liners??
Absolutely!
These are very moist and yummy. I found that they needed more than 5 minutes to cool. If you take them out of the pan too early, you lose a lot of the brown sugar/pineapple mixture.
Very good point!
Amazing! I ate 4 last night boyyyy they are delish when warm!!
I just had a hard time getting them to come out of the pan 🤔 .. more cooking spray next time?
Yes, they definitely need to be sprayed very well. Baking joy is what I use!
I made these today for an activity at work. DELICIOUS everyone loved them!!!
So glad you liked them!