Prepare the Dough: Beat the softened butter with both sugars in a big bowl until light and airy (around 2–3 minutes with a hand mixer). Crack in the egg and pour in the vanilla, then mix until everything is smoothly blended together. This creates the rich, buttery base of your cookies.
Mix the Dry Ingredients: In another bowl, combine the flour, baking powder, baking soda, salt, and cinnamon, and whisk until well blended. Gradually mix the dry ingredients into the wet ones, stirring gently until everything comes together. Be careful not to overmix, this helps your Cinnamon Roll Sugar Cookies stay soft and chewy.
Roll Out the Dough: Lightly flour a clean surface and roll out the dough into a rectangle, about ¼ inch thick. Take your time here, this will be the canvas for that signature cinnamon swirl.
Make the Cinnamon Filling: In a small bowl, blend the softened butter, brown sugar, and cinnamon together until the mixture is smooth and fully incorporated. Gently spread this over the rolled-out dough from edge to edge. The filling should reach every corner so each bite has that cozy, cinnamon-sugar flavor.
Roll It Up: Roll the dough into a tight log beginning at the longer side. Tightly cover the dough with plastic wrap and chill it in the refrigerator for 30 to 45 minutes so it can firm up and keep its form.
Slice and Bake: Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper. Take the chilled dough out of the wrap and cut it into round slices about half an inch thick. Place the cookies on the baking sheet, ensuring there's enough space between each one. Bake for 10 to 12 minutes, or until the edges have a subtle golden hue.
Cool and Glaze: Let the cookies sit on the baking tray for a few minutes, then transfer them to a wire rack to cool completely. If you'd like a sweet finishing touch, mix powdered sugar, a splash of milk, and a little vanilla extract to create a simple glaze. Drizzle over the cooled cookies and enjoy.