Maggie Monday: Pineapple Upside Down Cupcakes

There are a lot of normal deserts out there. Some even upside down ones. A few inside out ones. Any sideways ones? Let’s get back to the upside down kind with Maggie’s recipe below…

My mom used to make pineapple upside down cake for church events, and picnics. I loved the brown sugar topping with the buttery taste and the tangy sweetness of the pineapple. However, I don’t recall ever making one of these cakes myself. Just not in fashion any longer, I guess!

When I saw this recipe I thought the cupcakes were so cute, and decided to given them a shot. It was sort of fun to make this retro dessert! I felt very 1960’s cool!

These actually tasted great- just like I remember from my childhood. Mine didn’t turn out quite as pretty as the photos in the recipe, but I think if my muffin tin had a wider base, they might have looked better. Oh well!

Everyone sucked them down pretty quickly here at home. None left to share anywhere else!

Pineapple Upside Down Cupcakes

IMG_2709 - Featured Size

What you need:

1 can (20 oz) sliced pineapple, drained, reserve juice

1 box yellow cake mix

½ cup vegetable oil

3 eggs

1/3 cup butter, melted

2/3 cup packed brown sugar

12 maraschino cherries, halved


What you do:

Heat oven to 350°. Spray 24 regular size muffin cups with cooking spray. Cut each pineapple slice into 4 pieces and set aside. (I left them in the can, and just sliced them all at once)

In a large bow blend cake mix, oil, eggs, and pineapple juice with an electric mixer on low speed for about 30 seconds. Beat on medium speed 2 minutes, scraping bowl.

In a small bowl stir together melted butter and brown sugar. Spoon 1½ teaspoons of the butter mixture into each muffin cup. Then place 2 pieces of pineapple in each cup, then place a cherry half, cut side up, in the center of the pineapple pieces. Spoon ¼ cup of batter into each cup.


Bake for 20-25 minutes or until a toothpick inserted in the center of a cupcake comes out clean. Remove from oven and cool for about 5 minutes. Run a knife around the edge of each cupcake to loosen; invert onto a cookie sheet or platter. Serve warm.


Tags: , , , , , , , , , , , , , ,

Categories: Baking3, Dessert 2, Fruit 2, Guest-Maggie, kosher, Recipes, Vegetarian

Author:The Ranting Chef

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3 Comments on “Maggie Monday: Pineapple Upside Down Cupcakes”

  1. December 22, 2014 at 8:28 pm #

    I love pineapple upside down cake, so will try these cupcakes! Hope you have a wonderful holiday season, I will be up in Cleveland (Westlake) visiting my Mom soon… Wishing you the very Merriest Christmas and a Happy New Year, too! Smiles, Robin


  2. The Chaos Realm
    December 24, 2014 at 3:39 pm #

    I love pineapple….cake, pizza, with onions, on spaghetti…anything. This looks so scrumptious!



  1. Doctor Who-Themed Recipes and more delectable guilty (food) pleasures…! | The Realm of the Chaos Fairy - January 9, 2015

    […] Pineapple Upside-Down Cakes (for all your wibbly-wobbly, timey-wimey party gatherings): […]


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