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.
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Spoon 1 teaspoon melted butter into the bottom of each sprayed muffin cup.
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Spoon 1 tablespoon brown sugar in each muffin cup.
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Press a maraschino cherry into the center of the brown sugar in each muffin cup.
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Spoon a heaping tablespoon of crushed pineapple over the cherry and compact it with the back of a spoon into an even layer.
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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.
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Pour pineapple cake batter into the muffin cups, filling them almost to the top.
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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.
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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
These are much better than making a large 9×113 cake. I like the individual servings; ‘grab and go’ type thing.
Thank you and have a wonderful and enjoyable weekend.
You too Colleen!
Looks really good.
They look great! From scratch or not they must be very yummy!
I definitely need to try these!! So yummy and bright for summer!
This is one of my favorite desserts! Haha! I always burn my mouth on fresh oven goods. 🙂 Sometimes they are hard to resist. I never would have thought to do them individually like that. That’s perfect!
What a cute idea! I would love to try upside-down cakes in muffin tins sometime.
Yummy for my tummy!!
I made these the other night. Some in regular size cup cake pans and some in mini cup cake pans. They all came out delicious and very easy to make.
Yay! So glad to hear!
How long did you bake the mini cupcake tins for?
Thanks!
Having a dinner party next week, will make these for dessert , great idea.
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No kidding, people are here looking at a cake recipe. No need to interject a cult diet scripture. We’re just here to view the recipe and read reviews of people who’ve made it or have input on the tasty treat.
I’m making an upside down cake right now and came across this recipe, first I’d never thought of reserving the juice f/the canned pineapple to the cake mix. Second, the idea of making individual cupcakes sounds awesome. Definitely going to try this and let everyone know how it came out and what my thoughts are.
Thanks leanna!
These look great! I love baking with pineapple and I love how retro these are 🙂
I found this recipe on Pinterest and followed the link……hallelujah! I made two batches of these for my tiki party this weekend and I just know they will be a major hit. The flavor is amazing but worth the messy prep work. I wasn’t worried about overfilling my tins; I always cut off the poofy bottoms for a treat 😉
Great thinking!
Has anyone had a problem getting them out of the tin? Last week I made a corn muffin and sprayed the tin really good and they still stuck and broke apart.
I’We’re having a “Beat the Winter Blues” party this weekend and I would like to make these a day ahead. How should I store them to keep them moist/soft but not get overly gooey and sticky. Or do I just need to prep on Friday and bake on Saturday? Thank you!
I would just store them covered. If you’re worried about them getting too sticky refrigerate them.
Use my idea I sent below…bake in cupcake liners…easy to transport and you can heat them without a mess at all. the top of my 12cupcake tin was the only messy thing. Fun for the “eater’ to undo and be surprised when he flips his upside down cupcake! I hate messy cupcake tins! Mine are staying nice in a plastic storage container with lid. Staying moist but not in fridge overnight yet..
Made them for Easter, they are delicious! 🙂 Recipe is a keeper!
Thank you!
Made these tonight to take to an Easter lunch tomorrow. Followed your exact recipe. They are the perfect potion control size if you can eat just one. Thank you for the great recipe.
You’re welcome!
But, can I eat just one? I think not. They’re just too good!
I made them in 5.5 in pans and just increased the cook time since I also put a layer of cream cheese in the middle. Loved loved using the pineapple juice instead of water it did wonders for the flavor!
Cream cheese in the middle sounds divine!
Have these in the oven right now! My husband’s birthday choice. I did giant cupcake tin (6) so we will see if I made the right adjustments. I’m hoping they will look like small serving cakes. Thanks for the recipe, Christy!
Ooh! Hope it worked!
Colleen W, look on the inside of label of *ole pineapple. It has recipe for muffins.
I could not find this recipe earlier today when I thought I had saved it so I just winged it. I used paper cupcake liners and it worked great. Easier to transport to my daughter’s home and to church when I really need them. Take them out of the cupcake pan before they cool too much and I used a big spoon to be sure the bottom wasn’t too juicy but they were NOT. Warm if you like before serving and flip over ….remove cupcake paper liner. It worked great…Surprise in the bottom or I believe it is on the top! I will be making these often…..one of my favorite cakes anyway… and it was fun…I used the box mix too…easy peesy!
Thank you! Glad you enjoyed them!
I Need to make 150 desserts for an upcoming banquet . I tried the recipe and it is awesome and easy … My only problem is when I turn them over and place them on a plate for serving , ( I want them to look nice ) . Is there a way I can get them to lay flat w/out cutting the tops off. I guess what I’m asking is there a way I can get them to bake without puffing up at the top .
Hmm. I don’t. But you could slightly underbake them then they wouldn’t puff so much.
When I turned mine out, I placed a cookie sheet over the top of the muffin tin then flipped it. Next I pushed down until the muffin tin was touching the cookie sheet. That flattened them and made them all the same height.
Thanks for the tips!
Hello, I have the puffy top issue of baked goods solution. As soon as you take it out of the oven take a flat glass plate larger than the pan and place on poof. Slowly push down until the plate is level with the rim. It does not change the cake at all and your bottoms will be flat. I’ve used this method for 40 years.
Are your muffin pans deeper than normal? I noticed that with the heaping spoon full on crushed pineapple there wasn’t much room for batter in mine.
Hmm. No, they’re regular sized. That’s strange.
These are so yummy people will want 2. I made these for my minister and his wife. Now they are a weekly teat. The whole church wants some.
These are so yummy people will want 2. I made these for my minister and his wife. Now they are a weekly treat. The whole church wants some. I make them in the large muffin tin
I love hearing that!
Hi just wanted to say thank you my husband decided he wanted a Luau birthday party (Last minute) I’ve been frantically searching for easy desserts that I could make a LOT of pretty quick and I ran across your Recapie and couldn’t have been happier 🙂
Oh thank you! You are a good wife!
These are Awesome!! Made them for a friend’s wedding, have done a similar recipe, but this time used the crushed pineapple and much more of an improvement. Thanks!! I also bought foil ramekin dishes so that they could look like mini pineapple upside down cakes and not so much cupcakes. A tad bigger and wider. They came out so cute- and they didn’t stick to the foil at all. Definitely a keeper recipe. Thank you!!
Yay!! love hearing that.
Family couldn’t geat/eat enough. Perfect for traveling purposes. Thanks so much for sharing!
Good to hear!
I just made these upside down cakes for our family dinner. They look yummy and will serve as suggested with a sprinkle I’d confectionery sugar or whipped cream.I had extra batter so made 18 …. 6 with pineapple pieces as I had some fresh pineapple on hand but did make the others with crushed as suggested.
Hope you loved them!
Can you use this in a mini bunt cake pan?
I love these! Even better with finely chopped walnuts added before pineapple…
I made these today for a dinner party. The flavor was really good but I had a hard time getting them out of the pan. I was only able to make half of them look good enough to take with me. Iud there a trick to getting them out in one piece and to keep the bottom from sticking? I’d love to make them again.
Oh no! Well you could line them with liners. Or spray them really well with cooking spray? I’m so sorry. The longer it cooks the more the brown sugar will carmelize. So maybe cook them for less time.
Place a circle cutout of parchment paper in the bottom of each tin. I use it no matter what I’m baking and they always slide out perfectly.
I made these today for an activity at work. DELICIOUS everyone loved them!!!
So glad you liked them!
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!
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!
Can you use cupcake liners??
Absolutely!
I’m trying your pineapple upside down cupcakes recipe & adding a bit of pecan pieces to mine, ummm😋
I think that would be awesome!
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 just wondering if anyone has tried this recipe using a pineapple cake mix?
Ooh I bet that would be amazing.
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 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.
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!!
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!
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.
Just made these and my husband has a new favorite dessert!! Any tips on storing until the next day?!
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!