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Pineapple upside down cupcakes are a delicious treat your family will love.

Pineapple Upside Down Cupcakes

These pineapple upside down cupcakes are so good and fun to make. One of the most requested recipes on my site.

Pineapple upside down cupcakes is one of our most popular recipes.

1 box Pillsbury Moist Supreme Classic Yellow Cake Mix with pudding in the mix
1 (3.4 ounce) Vanilla Instant Pudding
3 eggs
1/3 cup oil
2/3 cup pineapple juice
1/3 cup milk
1 (8 ounce) can pineapple slices, drained (save juice)
1 (8 ounce) can crushed pineapple, drained (save juice)


1 stick butter, melted
1 cup brown sugar
maraschino cherries
 Spray muffin tins well with cooking spray.  Melt butter and sugar together on top of the stove. Add 1 tablespoon sugar mixture to each muffin cup. Next, put in 1 tablespoon crushed, drained pineapple or 1 pineapple slice in bottom of each cup. In a large bowl mix cake mix, pudding mix, eggs, oil, juice and milk with mixer.  Fill cups 1/2 to 3/4 full with cake mix.  Bake in preheated 350 degree oven for 25 minutes. Remove and let cool at least 10 minutes. Run a knife around the edges to loosen muffins from cups before removing.  Turn cupcakes upside down on a platter and add cherries. 
Note:  I used one regular 12 cup muffin tin and one large 6 cup tin to make these.  This way the recipe made 18 cupcakes.. If just using regular 12 cup tins, it should make about 24 cupcakes. You could use all crushed pineapple or all pineapple rings as well. I wanted to try them both ways to see how they turned out. I think the pineapple rings work better in the larger cup muffin tins.) These would be good topped with whipped cream and you could add nuts to the mix.   Enjoy!
 Pineapple Upside Down Cupcakes
If you like this recipe, you might also like my recipe for Raisin Cupcakes with Caramel Frosting.
Spicy Apple Upside Down Cupcakes
Red Velvet Cupcakes 
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  1. I made an upside down pineapple cake that was horrible. I mean bad. That’s it. I made this recipe. Except i used a Bundt pan. Crushed pineapples. I followed the recipe. This was an outstanding cake. Just what i wanted. Thank you so much for sharing.

    • The Southern Lady says:

      I am so glad this recipe worked so well for you Vanessa. Thank you so much for letting me know. This is one of our favorites! Have a wonderful week.

  2. I will be trying your recipe out this weekend using crushed pineapples. However, I would like to add pecans to the top of the mix. Would you suggest adding the pecans to the sugar mix or in with crushed pineapples?


  3. Just out of curiosity could u make these using sugar free ingredients?

  4. I loved your recipe! Is there a way to make it into a full cake? Thank you!

  5. Nice thinges to make thanks

  6. I know this was a while back. But, a friend just sent to me. I love, love your recipes….I get the on my email…thank you sooo much for all your great tasting and great looking recipes

  7. How did you get these to release? I have trouble sometimes when i do the cake version.

  8. CORRECTION ON MY EARLIER POST! I add the crushed pineapple AFTER the pineapple rings. Wasn’t thinking upside down. Lol

  9. These are delicious!!! I use crushed pineapple and pineapple rings when I make these and as a cake. We love lots of pineapple. So, I add the crushed pineapple before adding the rings. My sister and I have made the cakes like that for years. I love your recipes! Do you have a recipe book?

  10. Pudding mix? Is it made as instructions on the box or are we just putting the pudding powder in the cake mix?

  11. brenda mcinnis says:

    can’t wait to see their face at family meal. thanks so much.

  12. your site is just awesome and today I just made the coca cola cake and it turned out perfect and it is so delicious, thanks for the recipe.

  13. I made these for a fundraiser for Relay for Life. They were a huge hit all were sold and they were YUMMY!!!

  14. These look yummy and can’t wait to try them. They will definitely be added to my recipe collection.

  15. wanda f.grubbs alexander says:

    OH MY GOODNESS THESE LOOK DEVINE,My husband love pineapple upside down cake …he will enjoy these babies as well as my son-in-law..

  16. My 10 yr old and I made these this afternoon… So quick and easy! They are baking now and smell delicious! I only have one muffin pan so put the rest in a 9 inch cake pan… Hope it turns out! I’m going to lower the heat and cook a little longer

  17. Danielle Smith says:

    I found this recipe on pinterest and they were absolutely amazing. My family loved them and very moist! I am making them again for the fourth!! Awesome recipe!

  18. Marvell J. says:

    Okay, I’m confused! When do you use the topping? Is it put in the bottom of the muffin cup or is it added after they have been turned out of the muffin cup?

  19. Must they be eaten the same day or do they hold up well if you make the day prior? Thanks! Can’t wait to try!

  20. I am maki g these for dessert tonight and I am so excited!

  21. Judy…I made these today,and they were great…thanks for sharing…..:)

  22. Jeanne Keith says:

    I wrote on march 31 and asked a few questions. How often does the Southern Lady reply? I haven’t received a response yet. Thought maybe with Easter she was behind on mail. Thanks!

    • I usually reply the same day, Jeanne. Sometimes, the site goes down for repairs or something and e-mails are lost. I don’t have any pending ones here. I checked. What are your questions??? Did you ask a question on here or did you use the e-mail address on the blog???

      • Jeanne Keith says:

        Hi! I emailed at 4:28PM on March 31. I can see my comment on your website, so it must have gone through. If you don’t see it, let me know and I’ll send it again. It’s under comments. Thanks!

      • What recipe is the post under, Jeanne. There are hundreds of comments daily on here. I don’t know what recipe you are asking about.

  23. I also have made these in mini-muffin tins, takes awhile but my coworkers really loved them, they could just grab a few and go on. And I do so enjoy seeing them enjoying.

  24. Hi Judy,

    Wow….I can’t wait to try this! I love pineapple – this is a great summer dessert! I follow you on FB and Pinterest. I love all your yummy shares – thank you! I hope you are having a wonderful Saturday and weekend! Cheers

  25. Delores Hicks says:

    This calls for 1 tbsp. of sugar mixture to each muffin cup, what is the sugar mixture dont see it in recipe

  26. Paula ain’t got nothing on you girl!

  27. I think each of these look pleasing to the eye! Thank you for sharing.

  28. Tracey Simpson says:

    Just saw these 4 the first time , my family loves pineapple upside down cake so i cant wait to make the cupcakes there gonna luv them . ill get back to u with the results , thanx so much .

  29. Jeanne Keith says:

    These mini pineapple upside down cakes are delicious and very moist.
    However, what did I do wrong? I put a tablespoon of the brown sugar mixture in each cup and a tablespoon of crushed pineapple in each one. I ran out of both ingredients about 2/3 of the way through and had to mix up more and open another can of pineapple. Your recipe says 1 Tbsp. and I used a measuring spoon for this. I made 24 cupcakes and used a 16 oz. can of crushed pineapple. I took these to an Easter Brunch and they were a great hit! I will definitely make them again (just make 1 1/2 times the butter and pineapple, unless you have a suggestion). How can I also adapt this to making a whole cake? I have always made this cake in an iron skillet (as my southern Mother taught me), but it called for a 1 layer cake mix, such as Jiffy. Your cake is so much better I want to use it.
    Thanks so much for your help!

    • o.k. I found the questions. I used a large six cup pan that is the difference in the sugar mixture I am sure. I have made this in a 9 x 13 using the same measurements. You would make it just like you would make a regular cake because it uses a mix and pour into the pan. You might have to make more of the brown sugar topping for a long pan. I have never made this in an iron skillet.

  30. I can’t wait to make these for dessert they look amazing!
    I also wanted to tell you that this recipe was featured on my blog today for some last minute Easter dinner ideas. You can check it out here:

    Happy Easter

  31. Great Recipes, keep em coming.

  32. Linda Hathaway says:

    These are really fun to make and really delicious!! My husband and I love them!

  33. KATHEE ALLEN says:


  34. would you be able to freeze these? I am the only one in my family that likes pineapple upside down cake and I would love to make ind. ones like these and freeze them for later enjoyment

  35. Just a note to let you know that my youngest daughter (age 16) made these as the dessert for our New Years Dinner. We had a houseful of company and everyone *loved* them & the portion-size was just right.

    Made her feel good that she was able to make something that everyone liked. THANKS for the idea + recipe!

    • Love your story, Joe. So happy your daughter was able to make these and they turned out good for her. I try to make my recipes as simple and easy to understand as possible. I love hearing things like this, too.

  36. Vicki Boisselle says:

    I love these and so do my friends and neighbors. I prefer the small ones with crushed pineapple because they are the perfect size for the senior crowd that I am a member of. Absolutely amazing. They are like Pineapple upside down cake on steroids!!!!! Thank you!!

  37. Just made these and my whole house smells amazing! Cannot wait to try one and share them with mine and my husband’s workplaces! Thank you for the recipe 🙂

  38. I felt the need to write a review on this dessert, since I gotten rave reviews on it tonight. The cake had the perfect moisture levels you don’t need anything else to go with it. The brown sugar topping was the! When baked it made a beautiful caramel coating. This recipe is a keeper! Thank you!

  39. Oops! I only use one 12 cupcake pan. I’ll report back. Lol. They are quite large in the oven. 15 minutes to go…

  40. Hi Judy! I don’t think my last comment went through. I wanted to tell you that I have made many of your recipes and I love them! My mom is from the south so this is the cooking I’m used to and love. I’m making these cupcakes right now for 4th of July! Can’t wait to try them.

  41. Pingback: Pineapple Upside Down Cupcakes « Pintesters

  42. Thanks ever so for this recipe! I was a bit late for pineapple upside down cake day… finally tried it last night. I had some crushed pineapple in the pantry already, but not enough muffin tins, so we had a sheet cake. I will definitely do this again. My guys deemed it the best they’d ever had!

    Next time, though, I’ll be careful not to forget to add the pineapple before pouring in the batter, lol! I shoved it down in the batter, hoping it would sink to the bottom. It didn’t. The cake was VERY moist. 8-]
    Also, next time, I think I’ll use coconut milk and call it a pina colada upside down cake.

  43. Found these on pinterest and have made them 3 times. We love them! I even sent them to work with my husband at the fire dept.

  44. I am going to try these for our Easter bake sale – they look so pretty!!

  45. Cannot wait to make these. My family is gonna flip.

  46. Pineapple upside cakes are my dad’s favorite. I love the individual servings.

  47. These look delicious! I will definately be baking some of these soon.

  48. These cupcakes look divine Judy! What a great idea. I love individual servings in any style. =)

  49. What a great take on a classic. They look so moist.

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