Prepare the Streusel: Beat together 6 tablespoons of softened butter and ¾ cup of brown sugar until creamy. Mix in ¾ cup of flour, 2.5 teaspoons of pumpkin pie spice, and a pinch of salt until crumbly. Refrigerate.

Dry the Pumpkin: Spread ½ cup of canned pumpkin puree onto a plate, press with paper towels to absorb moisture until reduced to just under ¼ cup.

Mix Dry Ingredients: Whisk together 1.75 cups of flour, 1 tablespoon of pumpkin pie spice, ½ teaspoon of baking powder, ½ teaspoon of baking soda, and ½ teaspoon of salt in a large bowl.

Cream Butter and Sugar: In a mixing bowl, cream together ¾ cup of softened butter and 1 cup of brown sugar until fluffy.

Add Wet Ingredients: Mix in the 2 egg yolks and 2 teaspoons of vanilla extract, then fold in the dried pumpkin puree.

Combine Ingredients: Gradually incorporate the dry mixture into the wet mixture until just combined. Chill dough if sticky.

Shape Cookies: Portion out dough into 2-tablespoon balls and arrange on baking sheets. Indent tops and sprinkle with streusel.

Bake: Preheat oven to 350°F and bake for 11-12 minutes until edges are set. Cool on baking sheet.

Make Vanilla Glaze: Whisk together 1 cup of powdered sugar, 1 teaspoon of vanilla extract, and enough milk to reach drizzle consistency.