Pineapple Upside Down Cupcakes

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I can’t remember the last time I had a piece of pineapple upside down cake.  How wrong is that?  That might explain why my mouth was watering when I read through this recipe from The Southern Lady Cooks.  I recall my mom making a pineapple upside down cake that was far more complicated.  The box mix base certainly makes things easier and I am all about easy and delicious!

Pineapple Upside Down Cupcakes


  • 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


  1. Spray muffin tins well with cooking spray.
  2. Melt butter and sugar together on top of the stove. Add 1 tablespoon sugar mixture to each muffin cup.
  3. Next, put in 1 tablespoon crushed, drained pineapple or 1 pineapple slice in bottom of each cup.
  4. In a large bowl mix cake mix, pudding mix, eggs, oil, juice and milk with mixer.
  5. Fill cups 1/2 to 3/4 full with cake mix.
  6. Bake in preheated 350 degree oven for 25 minutes. Remove and let cool at least 10 minutes.
  7. Run a knife around the edges to loosen muffins from cups before removing.
  8. 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. These would be good topped with whipped cream and you could add nuts to the mix.   Enjoy!


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