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I have never had a pineapple upside down cake (I’ll pause so you can all appropriately gasp, as my family did)…….but they always look delicious so I put it on my Top 26 list of things to accomplish. As much I would love to eat an entire cake by myself, people have told me that it’s not good for me. Therefore, making a pineapple upside down cake seemed like it would be hard to share. Switch that cake into cupcakes and I only eat 3 and get people who have actually had a pineapple upside down cake to critique my work. They all loved it and said it was perfect (I like to think they aren’t biased at all)!

Total Time: 50 minutes        Cook Time: 20 minutes


6 tablespoons of Unsalted Butter

¾ cup Brown Sugar (tightly packed)

6 pieces of Maraschino Cherries

6 rings of canned Pineapples (get the 20 oz cans)


6 tablespoons of Unsalted Butter

½ cup of Milk

1 cup + 1 tablespoon of All-Purpose Flour

1½ teaspoon of Baking Powder

¼ teaspoon of Salt

2 Eggs

¾ cup of Sugar

½ teaspoon of Vanilla Extract

2 tablespoons of Pineapple Juice (from the can)

2 teaspoons of Maraschino Cherry Juice


(1) Heat the oven to 350 degrees.

(2) Place the butter and the brown sugar in a small saucepan and stir over medium heat until the butter has melted and the sugar has dissolved. Continue cooking, without stirring, for a few more minutes until bubbles start to appear and the sugar caramelizes. Remove sugar/butter mixture from heat and spoon about 1 tablespoon of the mixture into each cupcake slot. 

(3) Cut each pineapple ring into quarters and cut each cherry in half. Place the half of the cherry in the middle of the pan, the cut half facing up towards you. Put two quarters of the rings into each cupcake holder. (The pineapples won’t fit perfectly into the cupcake tins, but just try to gently push the edges of the pineapple into the brown sugar so that it sticks).

(4) Place the butter and milk for the batter in a small saucepan over medium heat. Warm the mixture, stirring occasionally, until the butter melts. Transfer to a small bowl to cool. 


(5) In a medium-sized bowl combine the flour, baking powder and salt until well blended. In a large bowl, whisk together the eggs, sugar and vanilla extract until smooth. Add the flour mixture and stir until flour is fully incorporated. Add the milk-butter combination, the pineapple juice and the maraschino cherry juice and stir until well combined. (Supposedly pineapple upside down cakes are naturally sweet, but if you want to cut down on that omit the pineapple juice, the cherry juice AND the 1 tablespoon of flour).

(6) Pour the batter evenly into the cupcake pan. Bake about 20 – 25 minutes until they are lightly browned, dry around the edges and pulling away from the pan a little. (For my oven it only took 20 minutes, but I believe it’s a bit faster than normal. Either way, I would recommend checking at around the 20 minute mark. You want the cake to still be moist).

(7) Let the pan cool for about 5 minutes. Use a butter knife to carefully loosen each cupcake from the edges and the bottom of the pan. Place a cookie sheet on top of the cupcake pan and invert the pan turning the cupcakes onto the cookie sheet. Slowly remove the cupcake pan. Let the cupcakes cool. 

(8) Enjoy!!!

Recipe Adapted from 
Joy of Baking