In a small bowl, combine the softened butter, brown sugar, and cinnamon. Mix until well combined.
Using clean hands, break the filling up into chunks of different sizes on a plate and place in the freezer for at least 30 minutes.
In a large bowl using a hand mixer cream together the butter, granulated sugar, and brown sugar until light and fluffy.
Add the eggs one at a time, mixing fully before adding the next. Add the vanilla and combine.
In a medium bowl combine the flour, baking soda, baking powder, and salt. Whisk to combine.
Add the dry ingredients to the wet ingredients. Mix until just combined.
Mix in the chunks of cinnamon roll filling until just combined.
Cover the cookie dough and chill for at least 30 minutes.
Preheat your oven to 350 degrees (F). Line a baking sheet with parchment paper or a silicone baking mat.
Make scoops of cookie dough about 1 ½ to 2 tablespoons in size. Place at least 3 inches apart on the baking sheet. Repeat with remaining cookie dough.
Bake the cookies for 10-12 minutes or until the edges are golden brown.
Allow the cookies to cool on the cookie sheet.