Step 1: Get that oven ready
Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper and set aside. This is where the cookie magic will happen.

Step 2: Mix the dry ingredients
In a medium bowl, whisk together the flour, baking powder, and salt. Simple but important—this combo gives your cookies structure and lift.

Step 3: Cream it up
In a large bowl, beat the softened butter with the granulated and brown sugars until light and fluffy, about 2–3 minutes. Add the egg and vanilla extract, then mix until smooth and dreamy.

Step 4: Combine the dry and wet
Slowly add the flour mixture into your wet ingredients, mixing just until a soft dough forms. Don’t overmix or you’ll lose that tender cookie vibe.

Step 5: Make the filling
In a small bowl, stir together the brown sugar, cinnamon, flour, and melted butter. It should look like the inside of a Pop Tart—sticky, sweet, and cinnamon-y.

Step 6: Fill and shape
Scoop a tablespoon of dough and flatten it slightly in your hand. Add about a ½ tsp of filling to the center. Top with another flattened tablespoon of dough and pinch the edges to seal the filling inside, then gently shape into a ball. Place on the prepared baking sheets, spaced 2 inches apart.

Step 7: Bake to golden
Bake for 10–12 minutes, or until the edges are just golden and the centers are set. Let them cool on the pan for 5 minutes before transferring to a wire rack. They’ll firm up as they cool, so resist the urge to eat them straight off the tray. (Or don’t. We won’t tell.)

Step 8: Glaze time
While the cookies cool, whisk together the powdered sugar, milk, vanilla, and cinnamon until smooth. Drizzle over the cooled cookies in messy zig-zags—this is a no-perfection-needed situation.