Pineapple Upside-Down Cupcakes

"Taken from the Duncan Hines website (credited to Stacy3099), these were a hit at our Thanksgiving gathering. Be forewarned: this made 24 regular sized cupcakes AND 12 mini cupcakes (<---the minis were ONLY batter: no pineapple, cherry, butter or brown sugar.) Mine baked for about 25 minutes, as I preheated the oven to 350, then dropped it to 325 after putting them in the oven! Enjoy!"
photo by Izy Hossack photo by Izy Hossack
photo by Izy Hossack
photo by alligirl photo by alligirl
photo by Lavender Lynn photo by Lavender Lynn
photo by diner524 photo by diner524
photo by diner524 photo by diner524
Ready In:
24 cupcakes


  • 1 duncan hines pineapple supreme cake mix
  • oil, and eggs called for on cake mix box
  • pineapple juice, in place of water called for on box (you don't have to use pineapple juice, I just think it enhances the flavor!)
  • 1 (20 ounce) can pineapple tidbits (save the juice!)
  • 1 12 cups light brown sugar
  • 12 cup butter, melted
  • 24 maraschino cherries


  • Mix the cake as directed on box, substitute pineapple juice from the canned pineapple in place of water called for in recipe. (Optional).
  • Melt the butter.
  • Spray cupcake pan with cooking spray. (Do not use paper liners!).
  • Place one teaspoon of melted butter in the bottom of each cup of the pan.
  • Add one tablespoon of brown sugar on top of the melted butter.
  • Place one cherry in the center.
  • Scatter the tidbits around the cherry to form a circle.
  • Add cake mix on top of the pineapple. (3/4 full).
  • Bake for 18-20 minutes or until cupcakes are cooked.
  • Let the pan cool on a cooling rack for about 5 minutes.
  • Run a knife along the inside edge.
  • Invert cupcake pan on the cooling rack.
  • Some of the brown sugar and pineapple might stay behind in the pan, just scrap it out and lay it on top of the cupcakes.

Questions & Replies

default avatar
  1. tinabina
    Has anyone made these with the canned sliced pineapple rings? Seems like that would be an easier way to do them.
  2. tinabina
    I wonder if these could be made with the canned pineapple rings? Seems like that would be easier. I will give them a try and let everyone know how they turn out or has anyone else done them this way?


  1. diner524
    OH WOW!!!!! These are fabulous!!! They are so moist and so full of flavor with using the pineapple juice. I made these in the very early morning hours and just before my DS and his girlfriend left to go out to lunch, she tried one and requested that she be able to take at least one home for her father that loves pineapple upside down cake. I followed exactly as written except that I made 12 jumbo sized cupcakes!!! They baked for 27 minutes and were perfectly done. I only had one cupcake that the pineapple stuck to the pan!!! Thanks so much for sharing this recipe, so much better than when you use a yellow cake mix!!! Congrats on your win in the game forum's Twelve Days Surprise Event!
  2. Lavender Lynn
    Really good flavor. I used regular muffin pans. Next time I would use large muffin pans. My pans ran over a little. Made for Best of 2012.
  3. njuniee_13122612
    Totally Awesome !! Absolutely a keeper to be made over and over ! Thank you so much for posting this recipe !!! Anyone reading this recipe and considering it.... DON'T HESITATE ! Break out your baking pans and stand back for the compliments and requests for the recipe !
  4. Spencer #2
    Really good cupcakes. I used crushed pineapple instead of the tidbits and it turned out very well. They didn't stick to the cupcake wrappers too bad. Just 2 of them became a little smushed when I gently tried to coax them out of the pan for serving. Those two just had to be sampled before the party!! I can't wait to make these again.
  5. Susan B.
    I made them in the larger muffin pan instead of a cupcake pan so there are only 12 instead of 24. The toppings fit better I think. I did 325 for 25 minutes and they came out perfectly done and look really nice.
    • Review photo by Susan B.


  1. Todd T.
    Try almond flour as a great carb friendly way to make a cupcake


Someone special recently gifted me with membership ~ I don't know who, but know they are special :D! Thank you! It is much appreciated.... My parents owned a grocery store when I was growing up, so there's my love of FOOD! My friends all love to drink, so there's my profession! I stopped bartending 5 years ago, when my son was born, but still 'do' private parties. DH and I did a 'Supper Club' for a while, but life kept getting in the way! I am a SAHM, to a rambunctious 5 y.o....I LOVE cooking and collect cookbooks and anything kitchen related! I'm kinda picky, but will just drop an ingredient or make a sub, so I can still try a recipe. I'm looking forward to many years of enjoyment here, and hope to participate in some events soon! Thanks to everyone for posting such great recipes, and if you review mine, just know that I appreciate the time and effort involved in the reviewing process! <img src=""> <img src=""> <img src=""> <a href=""><img src=""></a> <img src="" border="0" alt="Photobucket"> <img src=""> <img src=""> Partnered with chef#724631 <img src="" border="0" alt="Susie's Banner for Newest Zaar Tag"> <img src=""> <img src=""> <img src=""> Co-hosted: <img src=""> <img src=""> <img src="" border="0" alt="New Kids Participation Banner"> <img src=""> <img src =""> <a href="" target="_blank"><img src="" border="0" alt="BBBZWT%"></a> <img src="" border="0" alt="Photobucket"> <img src="" border="0" alt="Photobucket"> <img src="" > <img src="" border="0" alt="Photobucket"> <img src="" border="0" alt="Photobucket"> <img src=""> <img src=""> <img src=""> <img src="" border="0" alt="Photobucket"> <img src= "">
View Full Profile

Find More Recipes