1Start by making the streusel. Light a candle to set the mood for baking.
2Add 6 tablespoons of softened unsalted butter to a bowl.
3Add 3/4 cup of packed brown sugar to the bowl.
4Mix the butter and brown sugar together until combined.
5Add 3/4 cup of all-purpose flour, 2.5 tsp of pumpkin pie spice, and a pinch of salt to the butter and brown sugar mixture.
6Mix until the mixture resembles large crumbs.
7Next, prepare the pumpkin cookies.
8In a separate bowl, whisk together 1 3/4 cups of all-purpose flour, 1 tbsp of pumpkin pie spice, 1/2 tsp of baking powder, 1/2 tsp of baking soda, and 1/2 tsp of salt. Set aside.
9In a large bowl, cream 3/4 cup of softened unsalted butter and 1 cup of packed brown sugar together for 1-2 minutes until light and fluffy.
10Add 2 egg yolks and 2 tsp of vanilla extract to the creamed mixture and mix until pale and fluffy, about 1-2 minutes.
11Add 1/2 cup of dried canned pumpkin puree (after drying, it should be about 1/4 cup) and mix on medium-low speed to combine.
12Add the dry ingredients (flour mixture) to the wet ingredients and mix on low speed just until combined.
13Preheat the oven to 350°F and line two baking sheets with parchment paper.
14Scoop the dough with a 2 tablespoon cookie scoop and roll into balls.
15Transfer the cookie dough balls to the prepared baking sheet. Make a slight indent in the cookie dough balls using the palm of your hand.
16Measure out a slightly packed, heaping tablespoon of streusel topping and flip it on top of each cookie dough portion. Press down gently with the palm of your hand to better secure the streusel.
17Bake the cookies for 11-12 minutes.
18While the cookies cool, make the vanilla glaze by mixing 1 cup of powdered sugar, 1 tsp of vanilla extract, and 2-4 tsp of whole milk together in a small bowl until you achieve a drizzle-able consistency.
19Once the cookies are cool, drizzle the vanilla glaze over them.
To make the streusel, use your hands to mix until the mixture resembles large crumbs.
Dry the pumpkin puree by spreading it on a plate and pressing with a paper towel several times until it goes from about 1/2 cup to 1/4 cup and hardly any liquid transfers to the paper towel. This step is not optional.
If the cookie dough is too sticky, chill it in the fridge for 10 minutes.
When the cookies are straight out of the oven, scoot a large, round cookie cutter around them to give them a perfect circular shape.
For the vanilla glaze, start with 2 tsp of milk and add more as necessary to achieve a drizzle-able consistency.