Preheat oven to 350 degrees F.

Beat butter and sugar in the bowl of an electric mixer until smooth. Add egg and vanilla, mixing well until combine, about 2 minutes. Stir in flour, baking powder, salt, and cinnamon. Mix until dough comes together. Add in milk. If dough is crumbly, add milk 1 teaspoon at a time until it comes together.

Refrigerate dough while you make cupcake batter.

Cream butter and sugar in the bowl of an electric mixer until fluffy, about 3 minutes. Add eggs and vanilla and beat until combined.

Combine dry ingredients in a bowl. Add half of the dry ingredients, mixing until just combined. Add the milk. Once mixed, add remaining dry ingredients.

Line muffin tins with cupcake liners and add about 1 1/2 tablespoons (or however much you’d like for thicker cookie bottoms) of cookie dough in the bottom of the liner. Even out the dough with the back of a non-stick sprayed spoon. Using an ice cream scoop, drop batter (about 2 heaping tablespoons worth) on top of cookie dough mixture. Bake cupcakes at 350 degrees for 15-18 minutes.

Add butter and cream cheese in the bowl of an electric mixer and beat until fluffy and combined. Gradually add in powdered sugar and vanilla, mixing on medium speed and scraping down the sides of the bowl for 4-5 minutes. Finish with adding cinnamon, then mixing until combined once more. Frost cupcakes as desired and sprinkle with a little cinnamon sugar. Cupcakes should be refrigerated after about 1-2 hours of sitting out.