- 1 cup powdered sugar
- 2 tablespoons milk or cream
- ½ teaspoon vanilla extract
- ¼ teaspoon cinnamon (optional)
Servings: 20 cookies | Prep Time: 20 minutes | Chill Time: 30 minutes | Bake Time: 12 minutes | Total Time: 1 hour
Instructions
Step 1: Make the Cookie Dough
- In a large mixing bowl, cream together the softened butter, brown sugar, and granulated sugar until light and fluffy (about 2–3 minutes).
- Add in the eggs one at a time, mixing well after each addition, followed by the vanilla extract.
- In a separate bowl, whisk together the flour, baking soda, baking powder, and salt. Gradually add the dry ingredients to the wet mixture and stir until just combined. The dough should be thick and soft.
- Cover and chill the dough for 30 minutes to make it easier to handle later.
Step 2: Make the Brown Sugar Cinnamon Filling
- In a small bowl, mix together the brown sugar, cinnamon, and flour.
- Stir in the melted butter until the mixture resembles wet sand. This will be your gooey Pop-Tart–inspired filling.
Step 3: Assemble the Cookies
- Preheat your oven to 350°F (175°C) and line baking sheets with parchment paper.
- Using a cookie scoop or tablespoon, portion out the dough into 1½-inch balls. Flatten each ball gently in your hand.
- Spoon about 1 teaspoon of the cinnamon filling into the center of each flattened dough piece. Fold the edges up and around the filling, sealing it completely, then roll back into a ball shape.
- Place the filled dough balls on the prepared baking sheet, leaving about 2 inches of space between each cookie.
