Pineapple Upside Down Cupcakes

Throwing food away, especially fruits, vegetables and meat, really bums me out and I get kinda mad at myself for not making better use of it and being a better planner.  I’ll just get too excited about all the fruit that looks good at the store and wind up with way more than our family of 4 can consume before it goes bad.  Thankfully our son would eat nothing but fruit if we’d let him, so he helps out a lot when we have a surplus.  I’d bought a container of fresh pineapple for a fruit salad and had over half of it left.  I’d mixed some of it in with coconut yogurt (a terrific tropical summertime breakfast by the way) but wasn’t going to use it up in time that way.  Solution?  Cupcakes.


These were tasty and I’d make them again.  They are sweet, but not too sweet.  One cupcake for dessert was the perfect size.  The cake has great moist texture and all the cupcakes came out cleanly.  Some of the topping got stuck in the pan and so I had to fix a couple of them.  But overall these were pretty easy and quite lovely.

The original recipe, found here, uses canned pineapple.  I’m sure they’d be great with canned pineapple, but if you have access to fresh you should use it.  I ran out of cherries and so a few of the cupcakes just had pineapple…and I kind of preferred them that way.  While there is something wonderfully nostalgic and lovely about the cherry in the center of the pineapple ring I like the simplicity of the pineapple by itself.


The only change I made was to use a little less butter and brown sugar in the topping.  It calls for 1/2 tablespoon of butter and 1 tablespoon of brown sugar in each cup.  That just seemed like a lot to me.  I had to eyeball the butter, a little less than 1/2 tablespoon per cup.  And I used about 2 teaspoons of sugar in each cup.  I guess that’s not a huge change and it probably doesn’t make any difference…

I filled the cups 2/3 full.  While filling them up I realized that there was going to be a lot of batter left over, enough for 2 or 3 more cupcakes.  They baked right up to the top of the cups, so each one could have used a bit more batter, but better to have them too short than overflowing.  Enjoy!

Pineapple Upside Down Cupcakes




  • 6 tablespoons (3/4 stick) butter
  • 1/2 cup milk (2% or whole)
  • 1 cup flour
  • 1 1/2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 2 eggs
  • 3/4 cup sugar
  • 1/2 teaspoon vanilla extract


  • 6 tablespoons (3/4 stick) butter
  • 1/2 cup (2 teaspoons per cup) brown sugar
  • 6 maraschino cherries, halved
  • 4 fresh pineapple rings, cut into quarters


  1. Preheat the oven to 350°F.
  2. Place the butter and milk for the batter in a small saucepan over medium heat. Warm the mixture, stirring occasionally, until the butter melts.  Place in a bowl and let cool.
  3. While the butter cools, prepare the topping. Spray the muffin pan with nonstick spray.  Place a little less than 1 tablespoon of  butter into each muffin cup then sprinkle 2 teaspoons of brown sugar over the butter. Place the pan in the oven until the butter melts, about 3 minutes.
  4. Arrange the pineapple and cherry on top of the melted butter.  This may take a little finagling depending on the size of your pineapple pieces.  Set pan aside while you finish the batter.
  5. To finish the batter, whisk the flour, baking powder, and salt in a bowl. In a large bowl whisk together the eggs, sugar, and vanilla extract until smooth.  Add 1/3 of the flour mixture and stir just to combine.  Then add 1/2 of the milk mixture, stir just to combine.  Follow by 1/3 of the flour, the rest of the milk, then the rest of the flour, stirring between additions.
  6. Pour the batter into the muffin pan, dividing it evenly among all the cups. Bake the cupcakes until they’re lightly browned, dry around the edges, and pulling away from the pan a little, about 25 minutes.
  7. Transfer the pan to a rack to cool for 5 minutes. Use a butter knife to carefully loosen each cupcake from the edges and bottom of the pan, then place a cookie sheet over the top. Invert the pan, turning the cupcakes out onto the cookie sheet, then flip them pineapple side up to cool completely.  You may need to replace some of the pineapple if it sticks in the pan. Serve at room temperature.