1. How to Prepare the Streusel Topping

Start by making the streusel. In a medium-sized bowl, mix together the softened butter and brown sugar using an electric mixer on high speed until well combined and creamy. Add in the flour, pumpkin pie spice, and a pinch of salt, and mix until the mixture resembles large crumbs. You may need to use your hands to bring it together completely. Place the streusel in the refrigerator to chill while you prepare the cookie dough.

2. How to Make the Pumpkin Cookie Dough

Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper.

Drying the Pumpkin: This step is crucial! Spread the canned pumpkin puree on a plate and use a paper towel to gently press out the excess liquid. Repeat this process at least four times until the pumpkin reduces to about a 1/4 cup (~42 g). Properly dried pumpkin ensures the cookies bake correctly without becoming too moist.

Mixing the Dry Ingredients: In a small bowl, whisk together the flour, pumpkin pie spice, baking soda, baking powder, and salt. Set this mixture aside.

Creaming the Butter and Sugar: In a large bowl, cream the softened butter and brown sugar using an electric mixer on high speed for 1-2 minutes until light and fluffy. Add in the egg yolks and vanilla extract, and continue mixing on medium speed until pale and fluffy, about another 1-2 minutes. Next, add the dried pumpkin puree and mix on medium-low speed until fully incorporated.

Combining Wet and Dry Ingredients: Gradually add the dry ingredients to the wet ingredients, mixing on low speed just until combined. If the dough feels too sticky, chill it in the refrigerator for about 10 minutes before proceeding.

3. Baking the Perfect Pumpkin Coffee Cake Cookies

Use a 2-tablespoon cookie scoop to portion out the dough, rolling each scoop into a ball. Place the cookie dough balls onto the prepared baking sheets, spacing them about 2 inches apart. Gently press down on each dough ball to create a slight indent. Scoop a heaping tablespoon of the chilled streusel topping onto each cookie dough ball and lightly press down to adhere.

Bake in the preheated oven for 11-12 minutes. Once out of the oven, use a large, round cookie cutter to scoot around each cookie to achieve a perfectly circular shape. Allow the cookies to cool on the baking sheet for 10 minutes before transferring them to a wire rack to cool completely.

4. Preparing the Vanilla Glaze for Finishing Touch

While the cookies cool, prepare the vanilla glaze. In a small bowl, whisk together the powdered sugar, vanilla extract, and 2 teaspoons of milk. Adjust the consistency by adding more milk, 1 teaspoon at a time, until the glaze is smooth and pourable. Once the cookies are completely cooled, drizzle the glaze over them using a spoon or a piping bag. Let the glaze set before serving.