In a medium mixing bowl, combine 3 tablespoons of softened unsalted butter and 3/4 cup of brown sugar. Mix until creamy, then stir in 3/4 cup of all-purpose flour, 2 1/2 teaspoons of pumpkin pie spice, and a pinch of salt until large crumbs form. Cover and chill while preparing cookie dough.

Spread 1/2 cup of canned pumpkin puree on a plate and press gently with paper towels until it reduces to just under 1/4 cup. This step absorbs excess moisture.

In a large bowl, whisk together 1 3/4 cups of all-purpose flour, 1 tablespoon of pumpkin pie spice, 1/2 teaspoon each of baking soda and powder, and 1/2 teaspoon of salt.

In another bowl, beat 6 tablespoons of softened unsalted butter and 3/4 cup of brown sugar until fluffy, about 2-3 minutes. Add 2 egg yolks and 2 teaspoons of vanilla, mixing until well combined.

Blend the dried pumpkin puree into the butter-sugar mixture until smooth, scraping down the bowl.

Gradually add the flour mixture to the pumpkin mixture, stirring gently until just combined. Chill dough if too sticky.

Preheat oven to 350°F (175°C). Scoop dough and roll into 1-inch balls, placing them on a baking sheet lined with parchment paper. Press down gently and top generously with streusel.

Bake for 11-12 minutes until edges are slightly golden. Let cool on baking sheet for 10 minutes before transferring to a wire rack.

Whisk together 1 cup of powdered sugar, 1 teaspoon of vanilla extract, and 2-4 teaspoons of whole milk for glazing. Drizzle over cooled cookies.

Let the glaze set for a few minutes before serving.