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Brown Sugar Pop Tart Cookies

Brown sugar pop tart cookies wrap a cinnamon-brown-sugar filling inside soft cookie dough, then bake until the edges are lightly golden and the tops are set. A smooth powdered sugar glaze finishes these filled cookies with a sweet, nostalgic touch.
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Prep Time 25 minutes
Cook Time 17 minutes
Chilling and cooling 1 hour 10 minutes
Total Time 1 hour 52 minutes
Servings: 12 servings
Course: Dessert
Cuisine: American
Calories: 380
Ingredients Equipment Method Notes

Ingredients
  

For the cookies
  • 2.5 cups all-purpose flour
  • 1 tsp baking powder
  • 0.5 tsp salt
  • 12 tbsp unsalted butter softened; for the cookies
  • 0.75 cup light brown sugar packed; for the cookies
  • 0.25 cup granulated sugar
  • 1 egg large
  • 1 egg yolk large
  • 2 tsp vanilla extract
For the filling
  • 0.25 cup light brown sugar packed; for the filling
  • 1 tbsp unsalted butter softened; for the filling
  • 2 tsp ground cinnamon
For the glaze
  • 1 cup powdered sugar
  • 1.5 tbsp milk

Equipment

  • 2 18x13-inch sheet pan
  • 1 electric mixer

Method
 

Make the cookie dough
  1. Whisk the flour, baking powder, and salt together in a medium bowl.
  2. In a large bowl, beat 12 tablespoons of the butter with 3/4 cup of the brown sugar and the granulated sugar on medium speed until creamy, about 2 to 3 minutes.
  3. Beat in the egg, egg yolk, and vanilla.
  4. Mix in the flour mixture on low until no dry streaks remain.
  5. Cover and refrigerate the dough for 30 minutes.
Make the filling
  1. Stir the remaining 1/4 cup brown sugar, the remaining 1 tablespoon butter, and the cinnamon together in a small bowl until evenly combined.
Assemble and bake
  1. Preheat the oven to 350°F with racks in the upper-middle and lower-middle positions.
  2. Line two 18x13-inch sheet pans with parchment paper.
  3. Divide the dough and filling into 12 equal portions each.
  4. Flatten each dough portion into a disk.
  5. Enclose one portion of filling inside each disk and pinch the seam closed.
  6. Gently flatten each filled portion into a thick round.
  7. Arrange 6 cookies on each pan, at least 2 inches apart.
  8. Refrigerate the pans for 15 minutes.
  9. Bake for 14 to 17 minutes, switching the pans’ positions halfway through, until the edges are lightly golden and the tops look set.
Finish and glaze
  1. Let the cookies cool on the pans for 10 minutes.
  2. Transfer the cookies to a wire rack to cool completely.
  3. Whisk the powdered sugar and milk until smooth.
  4. Spread or drizzle the glaze over the cooled cookies.
  5. Let the glaze set for 15 minutes.

Notes

For neat filling, pinch each seam fully closed before flattening the cookies. Store in an airtight container at room temperature for up to 4 days; freeze for up to 2 months. A 1:1 gluten-free baking flour can be used in place of the all-purpose flour.