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Preheat oven to 350°F. In a large mixing bowl, beat 2 cups butter with an electric mixer on medium to high speed for 30 seconds. Add granulated sugar, baking powder, baking soda, salt, 1 teaspoon cinnamon and nutmeg. Beat until combined, scraping sides of bowl occasionally. Beat in eggs and 2 teaspoons vanilla until combined. Beat in pumpkin. Beat in as much of the flour as you can with the mixer. Using a wooden spoon, stir in any remaining flour.
Drop dough by heaping teaspoons 2 inches apart onto an ungreased cookie sheet. Bake for 10 to 12 minutes or until tops are set. Transfer cookies to a wire rack; cool.
For frosting, in a small saucepan cook and stir the remaining 1/2 cup butter and brown sugar over medium heat until melted and smooth. Transfer to a medium bowl. Stir in milk and remaining 1 teaspoon vanilla. Stir in powdered sugar until smooth.
Spread tops of cookies with frosting. If desired, sprinkle with additional cinnamon.