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Pineapple Upside Down Cookies 90.png

Pineapple Upside Down Cookies

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🍍 Pineapple Upside Down Cookies with a Sweet and Tangy Twist offer a delightful combination of juicy pineapple and maraschino cherries atop a soft sugar cookie base.
πŸͺ These cookies provide a perfect balance of caramelized sweetness and tropical flavors, making them ideal for any occasion.

  • Total Time: 45 minutes
  • Yield: 13 cookies

Ingredients

– 1 cup room temperature butter

– 1 1/2 cups granulated sugar

– 2 eggs

– 2 teaspoons vanilla extract

– 1/2 cup sour cream

– 3 cups flour

– 1 teaspoon baking powder

– 1 teaspoon cornstarch

– 1/2 teaspoon salt

– 13 canned pineapple slices

– 13 maraschino cherries

– 1/2 cup melted butter

– 1 cup packed light brown sugar

Instructions

1-Preheat your oven to 350 degrees Fahrenheit and prepare a mini round cake pan to set the stage for this easy bake. The process combines creaming butter and sugar for a fluffy base, then layering on that irresistible caramelized topping.

2-Cream butter and sugar: In a large bowl, cream together 1 cup room temperature butter and 1 1/2 cups granulated sugar until it’s light and fluffy that’s your dough foundation. Next, mix in 2 eggs, 2 teaspoons vanilla extract, and 1/2 cup sour cream until everything blends smoothly. Then, add 3 cups flour, 1 teaspoon baking powder, 1 teaspoon cornstarch, and 1/2 teaspoon salt; stir it all up to form the dough. In another bowl, combine 1/2 cup melted butter and 1 cup packed light brown sugar for the topping.

3-Building and Baking the Cookies: Now, spoon about one tablespoon of the brown sugar mixture into each pan cavity and spread it evenly. Top that with one canned pineapple slice and place one maraschino cherry in the center it’s like creating mini works of art. Scoop about three tablespoons of cookie dough onto each, flattening it with an offset spatula for even baking.

4-Bake and Cool: Bake for 25 minutes until the edges turn golden and the brown sugar bubbles up perfectly. Let them cool for 10 minutes, then invert onto wax paper to catch any run-off, and reposition pineapple slices if needed. For more details on using canned pineapple, check out similar fruit-based baking tips on our site. Cool completely before digging in, and store in an airtight container for best quality within 2 to 3 days.

Last Step:

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Notes

🍍 Use canned pineapple and cherries to enjoy this tropical treat year-round.
🍯 Use wax paper during inversion to manage the sticky caramelized glaze.
πŸͺ If pineapple sticks, carefully reposition it onto the cookie after baking for presentation.

  • Author: Brandi Oshea
  • Prep Time: 20 minutes
  • Cook Time: 25 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 1 cookie
  • Calories: 519
  • Sugar: 49 g
  • Sodium: 283 mg
  • Fat: 23 g
  • Saturated Fat: 14 g
  • Carbohydrates: 73 g
  • Fiber: 1 g
  • Protein: 4 g
  • Cholesterol: 86 mg