Pineapple Upside Down Cupcakes – a mini version of your favorite cake with butter, brown sugar, pineapple, and a cherry on top! Good warm or at room temperature so they’re great for parties or luaus.
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.
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 asstrong. 
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!
- 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
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Preheat oven to 350 degrees and spray 24 muffin cups with cooking spray.
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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.
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'm Christy Denney, The Girl Who Ate Everything. I can't be left alone with a warm cinnamon roll or chocolate chip cookie. 
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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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.
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!