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Pineapple Upside Down Sugar Cookies

A delightful twist on classic sugar cookies with caramelized pineapple and cherries, perfect for any occasion.
Print Recipe
Prep Time 15 minutes
Cook Time 18 minutes
Total Time 33 minutes
Servings: 12 cookies
Course: Dessert, Snack
Cuisine: American, Baking
Calories: 150
Ingredients Method Notes

Ingredients
  

For the Cookie Dough
  • 1 cup unsalted butter, softened Choose high-quality butter for best flavor.
  • 1 cup granulated sugar
  • 1 cup brown sugar, packed Light or dark brown sugar can be used.
  • 2 large eggs Room temperature eggs are ideal.
  • 2 teaspoons vanilla extract Use pure vanilla extract if possible.
  • 3 cups all-purpose flour Sifted for a lighter texture.
  • 1 teaspoon baking soda Ensure it’s fresh for proper leavening.
  • ½ teaspoon salt Enhances the flavor of the cookies.
For the Topping
  • 1 cup canned pineapple tidbits, drained Use tidbits for even distribution.
  • 10 pieces maraschino cherries For garnish, could use fresh cherries too.

Method
 

Preparation
  1. Preheat your oven to 350°F (175°C).
  2. In a large bowl, cream the softened butter, granulated sugar, and brown sugar together until light and fluffy, about 3-5 minutes.
  3. Add the eggs one at a time, followed by the vanilla extract, mixing until combined.
  4. In another bowl, whisk together the flour, baking soda, and salt. Slowly incorporate this mixture into the creamed mixture until a dough forms.
  5. In a muffin or cookie tin, place about a teaspoon of extra sugar in each well. Then, place a slice of pineapple in each well with a cherry on top.
  6. Scoop the cookie dough on top of the pineapple and cherry, covering them nicely.
Baking
  1. Pop your tray in the oven and bake for about 15-18 minutes or until the cookies are golden brown.
  2. Let them cool in the pan for about 5 minutes before flipping them out onto a cooling rack.
Serving
  1. Serve warm or at room temperature.
  2. Store leftovers in an airtight container at room temperature for up to a week.

Notes

Check for doneness around the 15-minute mark. You may swap pineapple for peaches or apples as desired.