First, preheat your oven to 350°F (175°C). Line a cookie sheet with parchment paper so the cookies don’t stick. This also helps them bake evenly.
In a large bowl, beat the softened butter, brown sugar, and granulated sugar together. You want the mixture to be light and fluffy. This step is key for creating that soft texture in the cookies. Add the egg and vanilla extract, then mix again until everything is fully combined.
In another bowl, whisk together the flour, baking soda, cinnamon, and salt. Combining dry ingredients separately ensures even distribution before they meet the wet mix.
Slowly add the dry mixture into the wet mixture, mixing until a dough forms. Once your dough is ready, gently fold in the chopped Pop-Tarts. Make sure they’re evenly spread throughout the dough for flavor in every bite.
Scoop the dough onto your lined baking sheet. Space them about 2 inches apart since they’ll spread a little. Bake for 10-12 minutes, or until the edges are golden brown and the centers are still soft.
While the cookies cool, whisk together the powdered sugar, milk, and cinnamon. Once the cookies have cooled completely, drizzle the glaze on top. Let it set before serving.
Serve warm or room temperature. I personally love them with a cold glass of milk. The mix of soft cookie, crunchy edges, and cinnamon glaze is so comforting.