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Pineapple Upside Down Sugar Cookies - Pineapple upside down cake in cookie form because everyone loves cookies! Soft sugar cookie bottoms with a ring of pineapple and cherry center all covered in a brown sugar glaze!
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4.34 from 12 votes

Pineapple Upside Down Sugar Cookies

These Pineapple Upside Down Sugar Cookies combine soft, thick sugar cookies with pineapple rings, maraschino cherries, and a buttery brown sugar topping. They're baked in a 6-cavity mini cake pan and flipped after baking for a fun cookie-sized twist on classic pineapple upside down cake.
Prep Time20 minutes
Cook Time25 minutes
Total Time45 minutes
Servings: 13 cookies
Author: Miranda Couse

Ingredients

  • 1 cup butter room temperature
  • 1 1/2 cups granulated sugar
  • 2 large eggs
  • 2 teaspoons vanilla extract
  • 1/2 cup full-fat sour cream
  • 3 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1 teaspoon cornstarch
  • 1/2 teaspoon salt
  • 13 canned pineapple slices
  • 13 maraschino cherries
  • 1/2 cup butter melted
  • 1 cup light brown sugar packed

Instructions

  • Preheat the oven to 350 degrees. Set aside the USA pan mini round cake pan.
  • In a large mixing bowl, add the butter and sugar and beat with a hand mixer on medium speed until light and fluffy.
  • Add in the eggs, vanilla extract, and sour cream. Mix until combined.
  • Add in the flour, baking powder, cornstarch, and salt. Mix until the cookie dough just comes together. Set aside.
  • In a separate bowl, stir together the melted butter and brown sugar until combined.
  • Add about a tablespoon of the brown sugar mixture to the bottom of each cavity. Spread it around to cover the bottom.
  • Add the pineapple slice on top of the brown sugar and the cherry in the center of the pineapple.
  • Add a 3-tablespoon cookie scoop of cookie dough to the top. Using an angled spatula, flatten out the dough.
  • Place into the preheated oven and bake for 25 minutes or until the edges are golden brown and the brown sugar is bubbling up the sides. 
  • Let cool for 10 minutes and then turn out onto a wax paper covered surface. Brown sugar will run all over, so the wax paper is necessary. If the pineapple sticks to the pan, just reposition it back on the cookie.
  • Let cool completely before eating. Store in an airtight container. These are best if ate within the first 2 - 3 days. 

Video

Notes

You can use 3 3/4 inch individual round cake pans instead of the USA Pan 6-cavity mini cake pan. 

Nutrition

Calories: 519kcal | Carbohydrates: 73g | Protein: 4g | Fat: 23g | Saturated Fat: 14g | Cholesterol: 86mg | Sodium: 283mg | Potassium: 188mg | Fiber: 1g | Sugar: 49g | Vitamin A: 775IU | Vitamin C: 5.4mg | Calcium: 66mg | Iron: 1.8mg
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