Follow these step-by-step instructions carefully for soft, chewy cookies with a perfect cinnamon swirl every single time. The process is straightforward and rewarding.

Step 1: Prepare the Cookie Dough
In a large mixing bowl, using a stand mixer with a paddle attachment or a hand mixer, cream together the 1 cup of softened butter and 1 cup of granulated sugar. Beat on medium-high speed for about 2-3 minutes, or until the mixture is light in color, fluffy, and has significantly increased in volume. Scrape down the sides of the bowl as needed. Add the room temperature egg and 2 teaspoons of vanilla extract, and beat again until everything is well combined, about 1 minute more.

Step 2: Combine Dry Ingredients
In a separate medium bowl, whisk together the 3 cups of all-purpose flour, 1 teaspoon of baking powder, and ½ teaspoon of salt. This step ensures that the leavening agent and salt are evenly distributed throughout the dough, which is essential for a uniform texture and rise.

Step 3: Finish the Dough
With the mixer on low speed, gradually add the dry ingredient mixture to the wet ingredients. Mix only until the flour is just incorporated. Be careful not to overmix at this stage; overmixing develops the gluten in the flour, which can lead to tough, dense cookies instead of soft and tender ones. The dough will be soft and slightly sticky.

Step 4: Roll and Fill the Dough
Turn the dough out onto a large piece of parchment paper. Dust the dough and a rolling pin lightly with flour to prevent sticking. Roll the dough into a large rectangle, approximately 12×16 inches and about ¼ inch thick. In a small bowl, stir together the ½ cup of packed brown sugar and 2 tablespoons of ground cinnamon for the filling. Brush the entire surface of the rolled-out dough with the ¼ cup of melted butter. Sprinkle the cinnamon-sugar mixture evenly over the buttered dough, leaving a small ½-inch border along one of the long edges. Gently press the filling into the dough with your hands.

Step 5: Roll and Chill the Log
Starting from the long edge without the border, tightly roll the dough into a log. The parchment paper can help you lift and guide the roll to keep it tight. The border you left clean will help seal the log shut. Once rolled, wrap the log tightly in the parchment paper or plastic wrap. Place the log in the refrigerator to chill for at least 2 hours, or up to overnight. This chilling step is absolutely critical. It solidifies the butter, which prevents the cookies from spreading too much in the oven and helps the swirl keep its shape.

Step 6: Slice and Bake
Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper. Remove the chilled log from the refrigerator and unwrap it. Using a sharp, thin knife or unflavored dental floss for the cleanest cut, slice the log into cookies that are about ½ inch thick. Arrange the slices on the prepared baking sheets, leaving about 2 inches of space between each cookie to allow for spreading.

Step 7: Bake to Perfection
Bake for 10-12 minutes, or until the edges are lightly golden brown and the centers are set but still look slightly soft. They will continue to firm up as they cool on the baking sheet. For a chewier cookie, err on the side of underbaking.

Step 8: Cool and Prepare the Glaze
Let the cookies cool on the baking sheets for 5 minutes before transferring them to a wire rack to cool completely. While the cookies are cooling, prepare the glaze. In a medium bowl, beat the 4 ounces of softened cream cheese and 2 tablespoons of softened butter with a hand mixer until smooth and creamy. Sift in the 1 cup of powdered sugar and beat on low speed until combined, then increase the speed and beat until smooth. Add the ½ teaspoon of vanilla extract and 1 tablespoon of milk or cream. Beat again until you reach a smooth, drizzling consistency. If the glaze is too thick, add more milk, one teaspoon at a time.

Step 9: Glaze the Cookies
Once the cookies are completely cool, use a spoon or a piping bag to drizzle the cream cheese glaze over them. Let the glaze set for about 20-30 minutes before serving or storing.