Preheat your oven to 350F degrees.
In the microwave or on the stovetop, melt the butter and then let cool completely.
In a large mixing bowl, whisk together butter and sugar until it’s smooth and incorporated.
Add in the eggs and vanilla extract and mix until combined.
Next, add in the flour, cinnamon, sea salt, and baking powder. Mix until everything is well combined.
Coat an 8in cast iron skillet with oil or butter. If you don’t have a cast iron you can always use an 8in cake pan!
Press dough into the skillet and bring it all the way to the edges. If the batter is too sticky, lightly wet your hands to help press it into the pan without sticking to you.
Bake in the oven for 25-30 minutes. If you want it more gooey, lean toward the shorter time. If you’d like it a little more done, let it cook for 30 minutes. To cut into slices, let cool completely before slicing.
While the cookie skillet is cooling, make the glaze. In a small bowl, using a hand mixer, beat the cream cheese and butter. Add in the powdered sugar and beat until combined. Next, add the milk 1 tbsp at a time until you reach the consistency you want. If you want a thicker frosting, lean toward 1-2 tbsp. If you want more of a glaze, lean toward 3-4 tbsp! Drizzle on the skillet, scoop and enjoy!