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Pineapple Upside Down Sugar Cookies

These soft and buttery cookies feature a caramelized brown sugar base topped with juicy pineapple and a cherry, embodying the essence of classic pineapple upside down cake in a fun cookie form.
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Prep Time 30 minutes
Cook Time 15 minutes
Total Time 45 minutes
Servings: 12 cookies
Course: Dessert, Snack
Cuisine: American
Calories: 150
Ingredients Method Notes

Ingredients
  

For the Cookie Base
  • 2 tablespoons Unsalted Butter, softened For greasing and making the dough
  • 1 cup Granulated Sugar For classic sweetness
  • 1/2 cup Brown Sugar Light or dark for caramelizing
  • 1 large Egg Room temperature for smooth mixing
  • 1 teaspoon Vanilla Extract And a hint of almond extract if desired
  • 2 cups All Purpose Flour Spoon and level for accuracy
  • 1 teaspoon Baking Powder Adds lift
  • 1/2 teaspoon Salt Balances the sweetness
For the Topping
  • 1 cup Pineapple, chunked Well drained and patted dry
  • 12 pieces Maraschino Cherries Optional for garnish

Method
 

Preparation
  1. Lightly grease a standard muffin pan and cut small parchment circles for easier flipping.
  2. In each muffin cup, add a dab of softened butter and a spoon of brown sugar, pressing gently.
  3. Place a small pineapple chunk or half a ring, plus a half cherry on top in each cup.
Making the Dough
  1. Cream the room temperature butter and granulated sugar until fluffy and pale.
  2. Mix in the egg, vanilla extract, and almond extract.
  3. In a separate bowl, whisk flour, baking powder, and salt, then add to the butter mixture.
  4. Chill the dough for 20 minutes if it feels sticky.
Baking
  1. Scoop a generous tablespoon of dough, flatten slightly, and place over the pineapple in each muffin cup.
  2. Bake until the edges are just golden, about 12-15 minutes.
  3. Cool in the pan for about 10 minutes before flipping.
  4. Run a thin knife around the edges, invert a tray over the pan, and carefully flip.

Notes

If a few cookies stick, they will still taste amazing. Enjoy warm cookies while plating the rest.