Pineapple Upside-Down Cupcakes

READY IN: 40mins
Recipe by alligirl

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!

Top Review by 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!

Ingredients Nutrition

  • 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


  1. Mix the cake as directed on box, substitute pineapple juice from the canned pineapple in place of water called for in recipe. (Optional).
  2. Melt the butter.
  3. Spray cupcake pan with cooking spray. (Do not use paper liners!).
  4. Place one teaspoon of melted butter in the bottom of each cup of the pan.
  5. Add one tablespoon of brown sugar on top of the melted butter.
  6. Place one cherry in the center.
  7. Scatter the tidbits around the cherry to form a circle.
  8. Add cake mix on top of the pineapple. (3/4 full).
  9. Bake for 18-20 minutes or until cupcakes are cooked.
  10. Let the pan cool on a cooling rack for about 5 minutes.
  11. Run a knife along the inside edge.
  12. Invert cupcake pan on the cooling rack.
  13. 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.

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