1. Preheat the Oven

Start by preheating your oven to 350°F (175°C). Line a baking sheet with parchment paper to prevent sticking.

2. Prepare the Cookie Dough

In a medium bowl, whisk together the flour, baking powder, baking soda, salt, and ground cinnamon. This helps to evenly distribute the leavening agents and spices throughout the flour.

In a separate large bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy, about 2-3 minutes. You can use an electric mixer for this step, which makes it easier to achieve that fluffy texture.

3. Add Egg and Vanilla

Add the egg and vanilla extract to the butter-sugar mixture. Mix until well combined. This step helps to incorporate moisture and flavor into the dough.

4. Combine Dry and Wet Ingredients

Gradually add the dry ingredients to the wet mixture, mixing until just combined. Be careful not to overmix, as this can lead to tough cookies.

5. Prepare the Filling

In a small bowl, mix together the softened butter, brown sugar, and cinnamon until it forms a paste. This will be your filling.

6. Roll Out the Dough

On a lightly floured surface, roll out the cookie dough into a rectangle, about 1/4 inch thick. The size doesn’t have to be perfect, but aim for something around 10×12 inches.

7. Spread the Filling

Spread the cinnamon filling evenly over the rolled-out dough. Use a spatula or the back of a spoon to smooth it out, making sure to get into the corners.

8. Roll It Up

Starting from one long side, carefully roll the dough into a log. Try to keep it tight but not so tight that the filling spills out. Once you’ve rolled it up, pinch the edges to seal the log.

9. Slice the Cookies

Using a sharp knife, slice the log into 1/2-inch thick rounds. You should get about 12-15 cookies, depending on how thick you slice them.

10. Bake the Cookies

Place the cookie slices on the prepared baking sheet, spacing them about 2 inches apart. Bake in the preheated oven for 10-12 minutes, or until the edges are lightly golden. Keep an eye on them, as baking times can vary depending on your oven.

11. Make the Cream Cheese Glaze

While the cookies are baking, prepare the glaze. In a medium bowl, beat together the softened cream cheese, powdered sugar, milk, and vanilla extract until smooth. Adjust the consistency by adding more milk if needed; you want it to be pourable but thick enough to cling to the cookies.

12. Cool and Drizzle

Once the cookies are done baking, remove them from the oven and let them cool on the baking sheet for about 5 minutes before transferring them to a wire rack to cool completely. Once they’re cool, drizzle the cream cheese glaze over the cookies.