These individual pineapple upside-down cakes are an eye-catching addition to my holiday dessert table. A boxed cake mix makes them easy to bake anytime.

Allrecipes Member

Recipe Summary test

prep:
20 mins
cook:
20 mins
total:
40 mins
Servings:
24
Yield:
24 servings
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Ingredients

24
Original recipe yields 24 servings
The ingredient list now reflects the servings specified
Ingredient Checklist

Directions

Instructions Checklist
  • In a small bowl, combine the brown sugar and butter; mix well. Spoon into 24 greased muffin cups. Drain pineapple, reserving the juice. Trim pineapple to fit the muffin cups; place one ring in each cup.

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  • In a large mixing bowl, combine the cake mix, eggs, oils and 1-1/4 cups of the reserved pineapple juice; mix well. Spoon over pineapple, filling each cup two-thirds full. Bake at 350 degrees F for 20-25 minutes or until a toothpick comes out clean.

  • Immediately invert onto wire racks to cool. Place a cherry in the center of each pineapple ring.

Nutrition Facts

215 calories; protein 1.8g; carbohydrates 33g; fat 8.7g; cholesterol 30.5mg; sodium 174.2mg. Full Nutrition
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Reviews (329)

Rating: 5 stars
01/07/2010
I had to make this recipe several times before I got it just right. Here is what I did and I recommend these changes highly! Use Duncan Heinz Pineapple Supreme cake mix with water instead of the yellow cake mix with pineapple juice. It is so much better. Use Texas Muffin pans sprayed liberally with cooking spray. Double the topping recipe of brown sugar and butter. Use whole pineapple rings and press them down into the muffin cups but make sure they are level so they don't make your cakes look lopsided. Put the cherries in before cooking. Just press them down into the middle of the pineapple ring. Bake as directed. Take them out of the oven and let them sit for exactly 5 minutes so the topping can cool a bit, otherwise it will all run off. No more than 5 minutes or they will stick. Run a knife around the edge of the cakes and invert. Make sure you put foil under the cooling rack as this is really messy when the butter/brown sugar topping starts to run. By allowing them to cool for 5 minutes, most of the topping will stay on. These are wonderful and so cute! I served them at a Bunko party and they were a big hit! Read More
(403)
Rating: 5 stars
11/06/2008
I made these for my brother's birthday and they were a huge hit. I used jumbo muffin tins which accommodated my self-made tidbit rings nicely. I also used pineapple cake mix sans pineapple juice (so I could drink it myself while baking, of course!) and added a bit of rum to the glaze since that's how I roll. Read More
(117)
Rating: 5 stars
06/29/2008
I just finished serving these, and with the advice of other cooks, made them an incredible sucess. I used the pineapple cake mix and followed the box instructions on it, using water instead of the pineapple juice in the original recipe. I am glad we did this, otherwise it would have been too sweet. I used a whole marischino cherry on the top of each...stem in to create height. I also made a delicious black cherry sauce and drizzled it over them. Absolutely will make these over and over. Too easy and absolutely delicious. I also used the muffin pans instead, making the pineapple slices fit perfectly. Thank you for sharing this! YUM! Read More
(111)
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Rating: 5 stars
04/19/2008
These are extremely yummy and are a very "cute" dessert - great for entertaining. You don't need to trim the pineapple rings - just push them down so they slope slightly up the sides of the cup. You can also put the cherry in the middle before you pour the batter on top. It makes the whole recipe even easier! Read More
(60)
Rating: 5 stars
03/31/2009
Very pretty dessert. I used a jumbo muffin pan and used the pineapple rings. If you do the same, you will also need a 8 oz. can of pineapple rings. There weren't enough pineapple rings in the 20 oz. can for 14 jumbo muffins. I used pineapple cake mix and the juice from the canned pineapple rings. There wasn't enough juice from the pineapple rings so I used water to make up the difference. Read More
(42)
Rating: 5 stars
01/12/2007
I love this recipe!! I made these for a bake sale & they were the first items to go--even before the chocolate!! I recommend using pineapple tidbits--they're easier to form the rings. I also sprayed my paper muffin cups with cooking spray & had no trouble getting the goodies out. They tasted great! Read More
(39)
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Rating: 5 stars
10/29/2006
I made these to take to work. I am very pleased. I used the pineapple tidbits like suggested, and placed the cherry half upside down in the butter/brown sugar mixture, then surrounded by the pineapple. I also loosened around each cake with a knife before inverting. They are very moist. You will love them!!! Read More
(29)
Rating: 3 stars
02/10/2008
the presentation was wonderful, however the taste was too sweet!, and plain. i made 12 jumbo cupcakes and 1 20 oz pineapple was enough. i also made this with pillsbury mix and only required 1 cup of juice/water. if you're using betty crocker, use 1 & 1/4 (just as the recipe calls for); for dh, i believe it's 1 & 1/3. then again... look for another recipe, and use the same cupcake concept. -- UPDATE (5 minutes later) -- i did a brief research on similar cakes and one of the recipe called for cinnamon in the batter. i've already baked the cake so i sprinkled the cinnamon on top. it was TASTY! so... keeping that in mind, i'll probably be making this again :). Read More
(25)
Rating: 5 stars
06/29/2007
i chose this recipe because i had a white cake mix begging to be used. so obviously, i omitted the yellow mix. i used fresh pineapple, which now that i've tasted it, probably wouldn't make a difference if you used canned, but i just LOVE fresh! i also put the cherries in the pineapple in one pan, and followed the recipes instructions on the other pan, and either way is good. the best thing about this recipe is the size!!!! i think the size is perfect for pineapple upside down cakes. prefect individual sizes, everyone gets some pineapple and a cherry. it was a very forgiving recipe. this has made my own recipe book and will be making it several times in the future! took the other posters advice about rum for my alcoholic friends, but i just poured some captain morgan over the chilled cakes and let it soak in. many compliments! Read More
(24)