Pineapple Upside Down Cupcakes

Photo taken by Nicole Ramos

The first time I ever tried this cake is when I had to make one for a close friend’s birthday.  It’s the only cake he loves and I could see why.  I looked and looked for the best possible recipe and decided on Paula Deen’s Pineapple Upside Cake recipe on Food Network.  I love Paula Deen! She reminds me so much of my grandmother when she cooks!

So, for this recipe, I cut it down and thought it would be cute as individual serving portions, rather than a large cake.  You’ll need a jumbo 6 cup muffin pan for this recipe.  If you only have a 12 cup muffin pan, I recommend substituting cans of diced pineapple instead of the sliced and arrange the dice pieces to reflect a pineapple slice.   This recipe should yield 16 individual cupcakes.

1 1/2 C all purpose flour
1/2 C  butter, plus 1/2 C (melted)
1 3/4 C   sugar
3 lg  eggs
1/2 tsp  pure vanilla extract
1 tsp  baking powder
1/8 tsp  salt
3/4 C  buttermilk
1 C  brown sugar
2 (20 oz.) cans of pineapple slices
1 (10 oz.) jar of maraschino cherries
Nonstick spray (I find that Pam’s Nonstick Baking Spray works best)
aluminum foil or parchment paper


  1. Preheat the oven to 350 degrees F. Spray the jumbo muffin pan with nonstick spray and set aside.
  2. In a large bowl, beat ½ cup butter at medium speed with an electric mixer until creamy. Gradually add the sugar, beating until fluffy. Add the eggs, 1 at a time, beating well after each addition. Stir in the vanilla and set aside.
  3. In a small bowl, add the 1 1/2 cups of flour, baking powder, and salt. Whisk to combine. Add the flour mixture into the egg mixture alternately with the buttermilk, beginning and ending with the flour mixture.
  4. Spoon the brown sugar (Approximately 1 tablespoon per cup) evenly into each muffin cup. Spoon the melted butter (about 1 teaspoon) equally over the brown sugar. Arrange the pineapple slices and cherries over the brown sugar. Reserve remaining pineapple slices and cherries for another use.
  5. Spoon batter into the cups until the cup looks about ¾ full, over the fruit and bake until a wooden pick inserted in center comes out clean, about 15 minutes. Let the cakes cool in the pans for 5 minutes. Cover wire racks with aluminum foil or parchment paper and invert the mini cakes onto wire racks to cool completely.

Viola!!  You are now ready to serve everyone something amazing!  These would be great to serve at a dessert party!

8 thoughts on “Pineapple Upside Down Cupcakes

  1. These look delish! My husband’s grandfather always requested Pineapple Upside Down Cake. He passed on about 7-years ago and I don’t think we’ve eaten it since. These look too good to pass up.

  2. I’m so sorry for your loss. For that same reason (a close friend of mine), passed away three years back, that I have not been able to make peanut butter cookies. I think it’s time for me to dust off that recipe! I hope this recipe brings new fond memories for you!

  3. in your ingredients you say 1-1/2 cup of flour, but in the directions you talk about 3 cups of flour. I thought 1-1/2 was not enough and thankfully saw the 3 cups before I finished mixing. Also, the 15 minutes was not even close for cook time. Mine are in 20 minutes right now and hopefully will be done soon. If you used very little muffin pans, a smaller cook time might work.

  4. Thank you so much for you feeback Katie! We definitely made the corrections for the flour, it should be 1 1/2 cups of flour. I’m not quite sure why it took over 20 minutes for your cupcakes, as this recipe as will all others have been made at least three times. I know when I bake at my friend’s house, her oven cooks at a cooler temperature, so I have to raise the temp by 25 -50 degrees. This recipe used a 6-muffin pan and I only filled the cup to where there was a quarter of space left. Let me know if you try it again!

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  6. Although the cupcakes taste fine they came out very short (made 16 as suggested). Made me question amount of flour indicated (1 1/2 cups). They also took a lot longer to bake than recipe indicates. Checked and my oven temp is accurate

  7. I recently made these and loved them! I followed the directions exactly except for the cook time. They took between 25-30 minutes, but believe me, they’re are worth every minute that you wait for them! Great recipe!!!

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