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Pineapple Upside Down Cupcakes

I love pineapple upside down cake. I especially love baking it when I don't feel like frosting a cake, or dealing with other things to make it pretty. Also, it has fruit right there in the name, so I don't feel bad if I have some for breakfast!

These cupcakes will be sticky and delicious! This recipe makes two dozen cupcakes and two mini-loaf pans, or about 30 cupcakes.


  • 1 3/4 cups butter

  • 1 3/4 cups dark brown sugar, packed

  • 3 3/4 cups flour

  • 1 cup white sugar

  • 2 20oz cans of pineapple in juice, in chunks or sliced

  • 7 eggs, separated

  • 2 teaspoons vanilla

  • 5 teaspoons baking powder

  • 1 teaspoon salt


  1. Preheat the oven to 400 degrees F. Spray 2-3 cupcake pans and set aside.

  2. In a small pan on medium-low heat on the stove, combine 3/4 cup of butter, 3/4 cup of pineapple juice from the cans, and the dark brown sugar. Heat and stir constantly for about 3 minutes after the butter has melted.

  3. Spoon about a tablespoon of this mixture into the bottom of each cupcake holder of the pans. You will have some left over; set this aside until after the cupcakes are done.

  4. Then, arrange pineapple in the brown sugar mixture in the pans. If you purchased sliced pineapple, you can cut the slices in any way they fit into the pan. (I cut each slice into 8 and put 3 pieces in the bottom of each cupcake.)

  5. Separate the eggs and lightly beat the egg yolks. Add the white sugar, vanilla, the remaining butter(melted), and the rest of the pineapple juice from both cans. (There should be about 1 1/4 cups of pineapple juice left.) Mix until combined.

  6. Mix in the salt and baking powder, then the flour.

  7. Beat the egg whites with a hand mixer on medium high for 2-3 minutes, or until they form soft white peaks. Gently fold into the rest of the batter.

  8. Pour the batter over the brown sugar and pineapples in the pans.

  9. Bake for around 20 mins. The cupcakes are done when they spring back after you touch them! Let the cupcakes cool for 10 minutes before taking them out of the pan.

  10. Which you wait for the cupcakes to cool, heat the butter/brown sugar/pineapple juice mixture from before until it bubbles. Pour some of this over each cupcake. You can put them all on a tray with raised edges to do this, or create raised edged by putting them all on heavy duty foil and folding it up. This helps the syrup to soak in!


  • The syrup at the end is totally optional, but I think it makes them really sticky and delicious.

  • You might really enjoy these warmed up with a cup of tea of the evening.

  • I didn't try it this time, but I'm absolutely certain that a little rum in the syrup would be amazing.

  • This is mostly based on this recipe from AllRecipes.

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