Pumpkin Coffee Cake Cookies

0 Pumpkin Cookie Dough: In a large mixing bowl, whisk together melted butter, sugar, and brown sugar until smooth. Add the egg yolk, vanilla, and pumpkin and whisk until well combined. Be sure to blot the pumpkin with paper towels to remove most of the moisture - you should be left with about half of the volume.
1 Add the flour, cinnamon, nutmeg, baking powder, baking soda, and salt, and mix with a rubber spatula just until incorporated. Cover the dough with plastic wrap and chill for 30 minutes.
2 While the dough chills, make the cinnamon filling and streusel topping.
3 Cinnamon Filling: In a small bowl, combine brown sugar, flour, and cinnamon. Mix in the melted butter until the mixture is fully combined. Set aside for at least 5 minutes to allow the mixture to firm up.
4 Portion the filling into one-teaspoon-sized pieces. Roll each piece into a ball, then press into a small disc. Place the discs on a piece of parchment and set aside.
5 Streusel Topping: In a medium bowl, combine the flour, brown sugar, and cinnamon. Add the melted butter and mix until all the ingredients are fully combined and the mixture is crumbly.
6 Preheat oven to 350°F and line 2 baking sheets with parchment paper.
7 Assembly: Once the dough has chilled, portion the dough using a #20 cookie scoop (about 3 Tablespoons or 2 ounces). Roll each scoop into a ball and flatten to about 3 inches in diameter. Place one disc of the cinnamon filling in the center of the flattened dough. Fold the edges of the dough up and over the filling, pinching and gathering them toward the center until the filling is fully enclosed. Gently roll the dough back into a smooth ball. Repeat with each of the cookies.
8 Place the cookies onto the prepared baking sheets, spacing them at least 2 inches apart. Lightly press down each dough ball to flatten the top. Then, using the rounded side of a tablespoon, press down in the center to create an indent. Add a heaping tablespoon of streusel topping into the indent and gently press it down.
9 Bake at 350°F for 12-14 minutes, or until the edges of the cookies and the streusel topping start to brown. Allow the cookies to cool for at least 15-20 minutes before adding the glaze.
10 Vanilla Glaze: In a small bowl, whisk together the powdered sugar, milk, and vanilla until well combined. Once the cookies have slightly cooled, use a whisk or a spoon to drizzle the glaze over the top of each cookie. Enjoy!