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Frosted Brown Sugar Cinnamon Pop Tart Cookies

Soft, thick brown sugar cookies with a gooey cinnamon brown sugar filling baked right into the center, topped with a cinnamon brown sugar frosting.
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Prep Time 40 minutes
Cook Time 12 minutes
Total Time 52 minutes
Servings: 16 Cookies
Course: Dessert
Cuisine: American
Calories: 260
Ingredients Method Notes

Ingredients
  

Filling:
  • ½ cup brown sugar packed
  • 1 tablespoon ground cinnamon
  • 2 tablespoons butter melted
  • 1 tablespoon all-purpose flour
Cookie Dough:
  • 1 cup unsalted butter softened
  • 1 ½ cups brown sugar packed
  • ¼ cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 3 cups all-purpose flour
  • 1 teaspoon baking soda
  • ½ teaspoon salt
Frosting:
  • 1 ½ cups powdered sugar
  • 2 to 3 tablespoons milk
  • ½ teaspoon ground cinnamon
  • ½ teaspoon vanilla extract
  • Pinch of salt

Method
 

  1. Stir together brown sugar, cinnamon, melted butter, and flour for the filling. Portion into small discs and freeze for at least 30 minutes.
  2. Cream butter, brown sugar, and granulated sugar until fluffy. Beat in eggs one at a time, then vanilla.
  3. Whisk flour, baking soda, and salt together, then mix into the wet ingredients until just combined.
  4. Scoop dough, flatten, place a frozen filling disc in the center, top with more dough, and seal into a ball.
  5. Chill assembled dough balls for at least 30 minutes.
  6. Preheat oven to 350°F. Bake for 11 to 13 minutes, until edges are set and centers look slightly underdone.
  7. Cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.
  8. Whisk together frosting ingredients and spread over cooled cookies.

Notes

  • Chilling the filling and the assembled dough are both essential to prevent leaking and spreading.
  • Don't overbake; cookies firm up significantly as they cool.
  • Unbaked assembled dough freezes well for up to 3 months.