Pineapple Upside Down Cupcakes
Pineapple Upside Down Cupcakes – a mini version of your favorite cake in cupcake form with butter, brown sugar, pineapple, and a cherry on top! These cupcakes are good warm or at room temperature so they’re a great recipe for parties or luaus.
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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.
This Pineapple Upside Down Cupcakes recipe has 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 a little bit of melted butter, 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, pineapple slices, and pineapple tidbits to see which one worked better. I liked the crushed pineapple and tidbits the best.
The tidbits give a nice flower shape but the pineapple flavor is not as strong as using crushed pineapple so your choice.
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 cupcakes onto waxed or parchment paper and you’re done!
WHAT’S THE BEST CUPCAKE PAN?
The Wilton Perfect Results Cupcake Pan is great for baking Pineapple Upside Down Cupcakes and is only $15 at Amazon. It only features 12 cups, so you’ll need two to make all 24 cupcakes at once. You can also bake half at once, which will take a little more time. I also like to use cupcake liners to make sure they don’t stick to the pan!
OTHER FRUIT RECIPES
- Easy Fruit Dip
- Poppy Seed Fruit Salad
- Grape Walnut Salad
- Peach Cobbler Recipe
- Fruit, Avocado, and Feta Salad
- Fruit Pizza
- Snickers Apple Salad
- Apple Crisp Pizza
OTHER CUPCAKE RECIPES:
- Rainbow Cupcakes
- Reese’s Peanut Butter Cupcakes
- Strawberry Puffcakes
- Strawberry Colada Cupcakes
- Strawberry Milkshake Cupcakes
- Funfetti Cupcakes
Pineapple Upside Down Cupcakes
Ingredients
- 1/2 cup butter, melted
- 1 1/2 cups brown sugar
- 24 maraschino cherries
- 1 (20 ounce) can crushed pineapple or pineapple tidbits (well drained but reserve juice)
- 1 (15.25 ounce) package yellow cake mix, (and ingredients called for on the package)
- 1 cup pineapple juice, (you just need as much pineapple juice as water called for on the cake mix package - see note)
- powdered sugar for dusting
Equipment
Instructions
- Preheat oven to 350 degrees and line 24 muffin cups with baking cups.
- Line a work surface with parchment or waxed paper.
- Spoon 1 teaspoon melted butter into the bottom of the pan 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 tablespoon of well drained crushed pineapple or about 5 pineapple tidbits over the cherry into an even layer.
- Mix cake mix according to the package directions, substitute pineapple juice for the water in the recipe. This may vary according to which cake mixture 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.
- Scoop pineapple cake batter into the muffin cups, filling them 3/4 of the way full.
- 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 for about 20 minutes. Unwrap cupcakes and invert onto a serving platter. Serve with pineapple and cherry sides up. Sprinkle cupcakes lightly with powdered sugar if desired.
Notes
*Some people like the look of pineapple tidbits better for this recipe. I tried both and it's really just personal preference.
Did you use standard cupcake tins or the larger muffin tins?
Standard for sure!
This was a fun recipe to make with a teen/preteen because of all the interesting but easy steps. Especially one who loves pineapple. I found that one 20 Oz can of crushed pineapple was not enough for 24 cupcakes, so we made 12 with crushed, 12 with tidbits. The teen preferred the crushed, I preferred the tidbits. May try making 1/2 the recipe next time.
Thanks! Great feedback
Made these for work so used cupcake liners. Sprayed per the instructions and they turned out perfectly and when liner removed they looked great. Used tidbits instead of crushed. Moist, delicious, and pretty. Will definitely make these again.
Thank you! So happy to hear that.
Really fun recipe, made them for the first time last night. Only thing is, the ones in the recipe look perfect, however I can not say the same about mine. I had some of the topping stick to the muffin pan, how do I prevent it next time?? Thank you!
I would use cupcake liners for a cleaner look!
I was skeptical on how they would flip out but it worked and they are delicious!!! I wish I could add the photo! Definitely a good to now!
So happy to hear that.
i’m back here for the third year in a row making these for my boyfriend’s birthday. they get better every time!
Awww that’s awesome.
These tasted good , but what a mess!!! One can of pineapple was not enough so had to back to the store for another can. Filling “almost to the top” made them spill over. Everyone of them had to be pried out and the topping was stuck on the pan. It took about 3 hours to Jake this simple recipe
Oh no I’m so sorry this hear this. Did you use a 20 ounce can? That should be plenty.
They are way better than expected! So excited to serve these at my party tomorrow 🎉🥳
So happy!
Love!!!! They are amazing and super easy.
This needs nothing additional to be everything you want. Everyone who had some was enamored. I don’t know what possessed me to add a cream cheese glaze on top. It doesn’t need it at all. Took it from 10/10 to “stop it, you don’t need to get fatter/10”, and I regret nothing. It was delicious also.
Haha that made me laugh out loud
I’m confused. In the paragraphs before the recipe you say not to use liners bc it will stick and then a little further down you say you like to use liners so it doesn’t stick.
Honestly. It depends on the liner.
I used a gluten free box mix. Worked great!
Good to know!
Delicious! Replace same amount of milk/water called for in cake mix directions with pineapple juice. Drain and squeeze out excess juice from pineapples. (I used 2 cans instead of 1). I’ll cut out parchment paper for cupcake pan bottoms from now on to prevent sticking. Such a clever adaptation and easy. Thank you!
I love this recipe because it’s personal also better with crushed pineapple ☺️👍
Thank you!
I’ve made these a few times and they’ve become my husband’s favorite dessert. Can I use cupcake liners in the muffin tins? Or will that be an issue for how the cupcake bakes?
I’ve use them but some people say theirs stick
I made these using oversized muffin tins. They turned out so good. Some of the brown sugar/pineapple/butter did stick in the pan,but no big deal, that happens when I make regular pineapple upside down cake., too. You just scoop it out and put it back on!
My question is, can these be frozen?
Sure! THey can be frozen.
Can you use a silicone pan instead of the metal pan?
Absolutely!
I’ve made this recipe a few times and my whole family loves it. Great recipe for me
Thank yoU!
I missed this important detai. “Just replace the water called for in your cake mix with pineapple juice.” What i got was Pineapple up side sponge cup cakes. Also there must be different size cupcake pans. Even with the combination of water and pineapple juice, there wasn’t enough “batter” to fill 24 cupcakes. Could you provide the cupcake diameter of the pans you used or expand on your ,”Pour pineapple cake batter into the muffin cups, filling them almost to the top.”?
Well shoot that’s not good! You are right maybe you have a jumbo cupcake pan? They all run a little different.
I love baking and trying new recipies but as soon as I see a packet cake as an ingredient I leave the site.
Yes. I usually do too but sometimes there’s a place for them!
I used pineapple box caked mix, many home cooks, and TV cooks, use boxed, jar, pre-cut ingredients. Everyone does not have the time ( or money) for from scratch. I love having options. These cupcakes are delicious!
Seems a shame to miss out on so many good recipes Sue! Too bad you don’t know how to substitute your own cake from scratch instead of the boxed. When I don’t have the convenience of boxed laying around or I know my recipes better, I substitute ‘from scratch’ cakes for the boxed. I’m just glad there’s recipes like this with shortcuts to help beginners get over their apprehension about phrases like ‘from scratch’ and get into baking. There are SO MANY people out there that didn’t have Home Ec in school or someone at home to teach them and I love that they can find recipes like these to show them they don’t have to be Martha Stewart to serve their family a home baked treat!
Hi, Sue! I generally leave a site too when I see “boxed cake mix” as an ingredient. However, I used “Miss Jones Organic Vanilla Cake Mix, 15.87 oz.” since there are very few ingredients in it. I’ve made this 3 times now and I believe I’ve now found how to make a delicious dessert with little cleanup. I use silicone cupcake liners, only 3/4 – 1 C brown sugar, and 3 cans crushed pineapple, drained very well. The ingredients are all organic. Follow the cake mix instructions, replacing the liquid with pineapple juice. When the cupcakes are baked, there might be some brown sugar in the liners. Scoop it up and place onto cakes.
I shouldn’t tell this BUT I took these cupcakes to a church function. They were labeled “pineapple upside down cupcakes”. They were demolished and everyone loved them. When I got home, I noticed a container that had unusual contents. I forgot to add the pineapple to the cakes. Lol. That’s how good they were! Try the recipe and I’ll be looking for your comments.
Terry G
Oh my gosh!! That is hilarious!! Wow!
Turned out great! Sprayed the tin first then added butter and brown sugar. They came right out and looked great.
Thanks!
Tasted great, but every one didn’t come out of the pan. I had to scoop out cherries, pineapple, and sugar butter out of tin and slap it back on the top of each cupcake. Also, filing cupcake tins to almost full with cake batter doesn’t really work either. Cake batter rises, so they all overflowed.
I tried these cupcakes with monk fruit. I’m sure they are delicious but it was way too sweet and the pineapple mixture looked great but turned an off white color after sitting a while. Do you think that’s because of the monk fruit.
Yes it is definitely because of the monkfruit
Made for my in-laws and they absolutely loved these! I am not a pineapple lover so I had to use their review.
haha awesome!
I loved these except when I inverted them the brown sugar stuck in the pan.
These came out really great as jumbo muffins. I ran out of pineapple so used up some raspberries and they disappeared too! Yummy recipe. Thank you for sharing
You’re welcome!
These were amazing. A couple of little things that seem to work for me. I used cherries with stems. Immediately after inverting I pressed a cherry into each muffin. They look so cute with stems. I also stirred a little cornstarch in the pineapple to reduce some moisture, thicken it a bit and keep it from running off when flipping.
Thank you!
How can I make these in the paper baking cups that stand alone since I won’t be able to invert them?
Sure!
These are awesome little cupcakes! Everyone loved them. they are very moist and flavorful, and super easy to make with a box cake mix.
Hopefully a helpful tip. I used silicon muffin pans, and they were very easy to remove.
Thank you!
Omg!!! These are so yummy 😋 I did a trial run using LG cupcake tin so I got 7 LG cupcakes from a cake mix(I used white cake mix it was what I had on hand). Needless to say I will be making these guys my daughters bday celebration. Super easy to follow directions amazing results!! Thank you!!!
Love hearing that Carol!
Just made these in jumbo cupcake pans. Put cut parchment paper circles in the bottom of the pans, and they came out ABSOLUTELY PERFECT!, Love, Love them,
Great tip Cheryl!
I love this recipe but I used a jumbo muffin pan so I was able to use the pineapple slices instead and did ur recipe to the T and OMG they came out so good … THANKS GIRL !!!! I’ll be ordering ur book soon 🙂
Aw thanks friend!
None of them cooked all the way through. The tops all came off. Followed the recipe completely. Was really excited too. Next time I’ll have to try a different way.
Sounds like you need to bake longer? Definitely should be cooked all the way through
These are good but a little too sweet for me. If I make them again I will decrease the amount of brown sugar.
These turned out perfect!! I used the non stick cupcake liners and nothing stuck to the bottom of them after I flipped them. The liners slid right off. Also since I filled them to the top they grew over and once I flipped them they looked more like little person size cakes. Super great recipe, everyone loved them!
Thank you!
DELICIOUS!!! I made them for my book club and everyone loved them. I used dark brown sugar and the flavor was amazing; however, it does get rather dark during baking. Light brown sugar would probably be a better choice. I will most definitely make these again!
Thanks for the tips!
They all did not come out perfect but honestly wasnt expecting them to. But they were delicious. I made them for a friend because she really wanted to try them so I made them for her. She loved them. Thank you for the recipe. I wanted something simple and thinners great!
These were delicious! Flavorful and a perfect size. Use the crushed pineapple! Also, I served these with whipping cream.
Awesome to hear!
I wonder if foil liners will work?
Yes! The foil liners worked perfectly.
Came out perfect. I just need to add the pineapple next time. Lol.
Oh my gosh
The topping stuck in the pan, but it was pretty easy to scrape out and plop back on the top of the cupcake. Girls at bunco raved about them and 10 yr old grandson loved them so much he thinks these will be better than a birthday cake next year.
I wonder if I can make these ahead and freeze them? I need to make several types of cupcakes for my daughter’s wedding in August.
YEs! You can!
The cupcakes taste good but, like many people, I had problems with the good stuff on the bottom sticking to the pan when I took the cupcakes out. And I sprayed well and even used extra butter. And I waited exactly 5 minutes before turning the muffin pans upside down to get the cupcakes out. Not sure I would make this recipe again.
Made these used the cupcake papers just sprayed them on the sides so along with butter mixture they came off almost perfectly little bit came off but smoothed back on with a knife. Granted papers were quite wet but did not soak into the cake. Cake mix I used was only 13.25 so only able to scrape out 20 cupcakes. Also had to cut the tops because to pointy to sit flat. Will probably stick with the cake version though.
Made this though the brown sugar and pinapple stuck to the bottom! Disappointed
I didn’t have enough pineapple juice, so I added the grenadine syrup from the maraschino cherries. It gave a little bit of a pep and added a little bit of color.
I have been doing it for years. Had to make upside down pineapple cupcakes for Mr. Tom at church for his 90th birthday!!! Miss Terry said that this way, he doesn’t eat too much at once and she can pop them in the freezer! ❤️
I make these in the mini muffin pan so they are little bite size treats. I just use 1/2 teaspoon butter, 1/T butter and pineapple and cut the cherries in half. Cook them for 13min. So freaking cute and delicious. Thank you for posting.
Edit* 1/2 Tablespoon brown sugar and 1/2 Tablespoon pineapple 😅🍍
You’re welcome!
As with other comments, the pineapple stuck in the pan. Taste was good. I tried the ring, it was too thick and had little cake, also came out wetter. The crushed was better but will try the parchment circles next time
Super disappointed. I followed the directions exactly and like other comments, the top (brown sugar and crushed pineapple stayed in the pan and did not release with the cupcakes. Groceries are very expensive and I do not like wasting them. I was making them for a church event and now need to research other options.
I’m sorry!
This sounds so good. My mom always made Upside down cake! The store I use does not sell 18 oz cake mix ~ only 15 oz. How do I made adjustments to the recipe using the 15 oz mix?
You don’t need to adjust anything. The cake mix is just made according to the package directions.
These are delicious! I cut small parchment circles for each muffin to help with sticking. I still had to run a toothpick around the sides for them to release after cooling for a while. But once they released, they were perfect.
**Should these be stored in the fridge?**
I do not store them in the fridge but if leaving out for a while then probably is a good idea
Going try these in a silicone cupcake dish. See if they come out better than a pan.
Did it work with the silicone cupcake dish. Very curious for out summer luau.
These were absolutely perfect for my daughters Moana themed party. Everyone loved them-they were delicious, a total hit!
So glad you liked it!
Made these and they were a hit with my family and neighbors. So much so my daughter wants me to make this as a double layer cake for her birthday. Any suggestion as to how long to bake it in a standard round pan?
Shoot I would go with what it says on the back of the box you are using.
Great recipe! Two adjustments I made.
1 After spraying the pans I had cut the bottoms off cupcake liners and put in the bottom to prevent sticking.
2 After they cooled I ran a sharp paring knife around the side.
The cupcakes stayed together and came out with no problems
the bottom didn’t cook on mine. they came out all loose and moist on the bottom
18.25 oz cake mixes aren’t generally available any longer. Another site suggests adding 1/3 cup of flour. And they now only call for one cup of liquid for the 15.25 oz size. I also used parchment circles in the pans after seeing the comments about sticking.
Proportions are off. All cup tins were overfilled if i followed this.. And what about a heads up to use pineapple juice BEFORE the mixing of batter per box…
The recipe said to see the notes about the pineapple juice.
Delicious, picture prefect!
Clear, easy directions on the recipe.
Was a joy to make!😊
Thank you!
Has anyone ever made large cupcakes in a six muffin tin? If yes, how long did you bake them?
Followed recipe exactly as written. They came out perfect! They taste and look beautiful.
Thank you!
I made a double batch for a luau-themed meal. I didn’t taste one but my husband did and said they were delicious. I used a Duncan Hines Pineapple cake mix, and used the liquid from the crushed pineapple.
I sprayed the pans a ton to help prevent the toppings from sticking, sadly it still stuck. I also only had dark brown sugar on hand, I don’t recommend this – they looked burnt. I squeezed the extra liquid from the crushed pineapple, maybe leaving some of that liquid would have helped the sticking. I’ll try that next time.