In a large bowl, beat butter on high for 30 seconds. Add the dry ingredients to the butter, mixing well. Add the eggs, vanilla, and pumpkin; beat to combine. Gradually add the flour; mixing until the flour is incorporated and the batter is stiff. Drop individual tablespoons of batter onto an ungreased baking sheet, spacing the cookies 2 inches apart.
Bake at 350 for 10-12 minutes or until the tops are set. (If you want giant cookies, scoop out ΒΌ of batter, space 2 inches apart, and bake for 13-15 minutes.) Remove from oven and cool on a wire rack.
In a medium saucepan, heat the butter and brown sugar until melted. Once the mixture is smooth, stir in the milk and vanilla; then beat in the confectioners' sugar. Frost and sprinkle the cookies with some additional cinnamon, if desired.
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