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Brown Sugar Pop Tart Cookies

Nostalgia in a bite! These incredible cookies feature a soft cinnamon-spiced cookie dough stuffed with a gooey, molten brown sugar filling, all topped with a sweet cinnamon glaze. Just like your favorite childhood toaster pastry, but better.
Print Recipe
Prep Time 30 minutes
Cook Time 12 minutes
Total Time 1 hour
Servings: 12 cookies
Course: Dessert, Snack, Sweet Treat
Cuisine: American
Calories: 385
Ingredients Equipment Method Notes

Ingredients
  

Cookie Dough
  • 1 cup Unsalted butter Softened to room temperature
  • 0.75 cup Dark brown sugar Packed
  • 0.5 cup Granulated sugar
  • 2 large Eggs Room temperature
  • 2 tsp Vanilla extract
  • 3.25 cups All-purpose flour Spooned and leveled
  • 1 tsp Ground cinnamon
  • 1 tsp Baking soda
  • 0.5 tsp Salt
Gooey Filling
  • 0.75 cup Dark brown sugar Packed
  • 1 tbsp All-purpose flour
  • 1 tbsp Ground cinnamon
  • 2 tbsp Unsalted butter Melted
Cinnamon Glaze
  • 1.5 cups Powdered sugar Sifted
  • 0.5 tsp Ground cinnamon
  • 0.5 tsp Vanilla extract
  • 2-3 tbsp Milk Or heavy cream, as needed for consistency

Equipment

  • Stand mixer or hand mixer
  • Baking sheets
  • Parchment paper

Method
 

  1. Make the filling: In a small bowl, mix the dark brown sugar, flour, and cinnamon. Add melted butter and mix until it resembles wet sand. Roll into 12 small balls, place on a plate, and freeze for 15-20 minutes.
  2. Make the dough: Beat the softened butter, dark brown sugar, and granulated sugar until pale and fluffy (2-3 minutes).
  3. Add the eggs one at a time, mixing well after each. Stir in the vanilla extract.
  4. In a separate bowl, whisk the flour, cinnamon, baking soda, and salt. Gradually add dry ingredients to wet, mixing until just combined. Do not overmix.
  5. Take about 2 tablespoons of dough, flatten it into a disc, and place a frozen filling ball in the center. Carefully fold the dough around the filling, pinching seams tightly to seal. Roll into a smooth ball.
  6. Chill the stuffed dough balls in the fridge for 30 minutes. Preheat oven to 350°F (175°C) and line baking sheets with parchment paper.
  7. Bake for 11 to 13 minutes until edges are set but centers are still soft. Let cool on the baking sheet for 10 minutes before moving to a wire rack to cool completely.
  8. Make the glaze: Whisk powdered sugar, cinnamon, vanilla, and 2 tablespoons of milk. Add more milk drop-by-drop if needed until spreadable but thick.
  9. Spoon a tablespoon of glaze onto each completely cooled cookie. Let sit for 30-45 minutes until the icing hardens.

Notes

Important: Ensure the seams of your dough are pinched perfectly tight around the filling. If there are cracks, the brown sugar center will leak out during baking!