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Combine all dry ingredients for the cookie dough in a bowl: 1 ¼ cup all-purpose flour, ½ tsp ground cinnamon, ¼ tsp baking powder, ¼ tsp fine salt, and ½ tsp baking soda.
In a separate bowl, add ½ cup room temperature unsalted butter, ½ cup granulated sugar, and 2 tbsp light or dark brown sugar. Mix until combined.
Add 1 tsp pure vanilla extract and 1 large room temperature egg to the wet ingredients and mix until well combined.
Gradually add the dry ingredients to the wet ingredients, mixing until a dough forms.
In a separate bowl, combine 2 tbsp unsalted softened butter, 2 ½ tbsp packed light or dark brown sugar, 2 ¼ tsp all-purpose flour, and 1 ½ tsp ground cinnamon to make the cinnamon roll filling.
Freeze the cinnamon roll filling for 5 to 10 minutes until it's hard to the touch.
Scoop out half of the cookie dough into a separate bowl.
Add the hardened cinnamon roll filling on top of the scooped cookie dough.
Cover the filling with the remaining half of the cookie dough.
Scoop the combined cookie dough and cinnamon filling into balls and place them on a baking sheet.
Bake the cookies in the oven for 8 to 10 minutes.