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Glazed Pineapple Upside Down Cookies stacked on a marble plate with pineapple slices.

Pineapple Upside Down Cookies

5 from 1 vote
Aliana Recipes
Golden, buttery rounds topped with caramelized fruit and a bright cherry center offer a tropical twist on a classic dessert. These soft treats feature a tender crumb and a sweet, syrupy finish that makes them a standout addition to any platter.
Prep Time 20 minutes
Cook Time 15 minutes
Total Time 35 minutes
Servings:12 people
Course:Dessert
Cuisine:American
Calories:210kcal
Cost:$9

Ingredients
  

  • 1 box yellow cake mix Provides a consistent, fluffy base
  • ½ cup unsalted butter, melted Adds richness to the dough
  • 2 large eggs Binds the ingredients together
  • 12 slices canned pineapple rings Drained and patted dry
  • 12 whole maraschino cherries Placed in the center of each ring

Equipment

  • 2 Baking sheet Line with parchment paper
  • 1 Mixing bowl For the cookie dough
  • 1 Cooling rack To prevent soggy bases

Method
 

  1. Combine the cake mix, melted butter, and eggs in a large bowl until a thick, pliable dough forms. This mixture serves as the sturdy foundation for the fruit toppings.
  2. Scoop portions of dough onto a lined baking sheet and flatten them slightly to create a wide base for the fruit. The dough should be large enough to hold a full ring without overflowing.
  3. Press a fruit ring and a cherry firmly into the center of each dough mound to secure them before baking. This step ensures the toppings stay in place as the dough rises and expands. Should the fruit be fresh or canned? Canned fruit is preferred for this recipe because it is pre-softened and carries the consistent sweetness needed for a caramelized finish.
  4. Bake at 350°F for fifteen minutes until the edges are lightly toasted and the centers are set. You will notice the fruit appearing glossy and the dough becoming a pale golden color when finished.

Nutrition

Serving: 75g (1 cookie)Calories: 210kcalCarbohydrates: 32gProtein: 2gFat: 8gSaturated Fat: 5gPolyunsaturated Fat: 0.5gMonounsaturated Fat: 2gCholesterol: 45mgSodium: 240mgPotassium: 45mgFiber: 1gSugar: 18gVitamin A: 4IUVitamin C: 10mgCalcium: 40mgIron: 0.8mg

Notes

Patting the fruit slices dry with a paper towel prevents excess moisture from making the dough soggy during baking. I often use a light sprinkle of brown sugar under the fruit to enhance the caramelization process.