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5 from 15 votes

Pineapple Upside Down Cupcakes

These pineapple upside down cupcakes are one of the most popular recipes on my website. Everyone loves them!
Prep Time20 mins
Cook Time25 mins
Total Time45 mins
Course: Dessert
Cuisine: American, southern
Keyword: Pineapple Upside down cupcakes
Servings: 18 cupcakes
Author: The Southern Lady Cooks


  • 1 box Pillsbury Moist Supreme Classic Yellow Cake Mix with pudding in the mix
  • 1 (3.4 ouncVanilla Instant Pudding
  • 3 eggs
  • 1/3 cup oil
  • 2/3 cup pineapple juice
  • 1/3 cup milk
  • 1 8 ounccan pineapple slices, drained (save juice
  • 1 8 ounccan 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.


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.