Prepare the streusel by beating cold unsalted butter and brown sugar until combined. Add flour, pumpkin pie spice, and salt, mixing until coarse crumbs. Chill for 30 minutes.

Spread canned pumpkin puree on a plate and press out excess moisture with paper towels until approximately 1/4 cup of dried pumpkin remains.

In a large bowl, whisk together all-purpose flour, baking powder, baking soda, pumpkin pie spice, and salt.

Cream softened butter and brown sugar until light and fluffy. Add egg yolks and vanilla extract; mix well.

Fold dried pumpkin puree into creamed mixture, then gradually mix in dry ingredients until just combined.

Scoop dough into balls, place on a baking sheet, create an indent, and top with chilled streusel.

Preheat oven to 350°F (175°C). Bake cookies for 11-12 minutes, watching them closely.

Cool cookies on baking sheet for 10 minutes, then transfer to wire rack. Prepare glaze by whisking together powdered sugar and milk, then drizzle over cooled cookies.