Step 1

Using a stand mixer with a paddle attachment (or a hand mixer), add the powdered sugar and salt to the bowl and mix to combine.

Step 2

Add the cold butter pieces and beat on low to start, then increase the speed. Beat until the butter and sugar form almost like a paste. Scrape down the sides of the bowl as needed.

Step 3

Add in the egg, egg yolk, vanilla extract and almond extract (if using).

Step 4

Add the flour and baking powder and mix just until combined. If the dough seems dry, add a splash of milk.

Step 5

Divide the dough in half.

Step 6

Place each half of dough on a sheet of parchment paper. Place a second sheet of parchment paper on top of each half of dough.

Step 7

Using a rolling pin, roll out each half of dough between the 2 sheets of parchment until ~⅜ inch thick. (Tip: ⅜ inch thick is right in between ¼ and ½ inch thick.) I like them a little thick, so they have a nice chew!

Step 8

Then, freeze the dough until cold (20-30 minutes or longer if needed).

Step 9

Meanwhile, mix together the pumpkin filling ingredients until smooth. (Or you can use a hand mixer if you prefer.)

Step 10

In a bowl, stir together all the crumble topping ingredients until the dough comes together. You should be able to pinch it between your fingertips and it stays together. If not, add a little more melted butter.

Step 11

Preheat the oven to 350°F. Line a couple baking sheets with parchment paper.

Step 12

Using a 2 ½ inch circular cookie cutter, cut the cookies into circles.

Step 13

Spread some of the pumpkin filling on each cookie, spreading it all the way to the edges of the cookie.

Step 14

Top with a generous amount of the streusel crumble topping. Don’t be shy!

Step 15

Bake for ~9-11 minutes or until you can start to see the edges begin to brown and the crumble looks a little golden. Careful not to over-bake.

Step 16

Remove from oven and allow to cool on cookie sheet for a couple minutes then carefully transfer to a wire rack.

Step 17

Mix together the cinnamon and sugar until combined.

Step 18

Whisk together the ingredients for the glaze.

Step 19

Sprinkle a little of the cinnamon-sugar topping on top of the streusel, and then drizzle the glaze over the cooled cookies.

Step 20

(Optional) You can add a little dollop of piped whipped cream on top of the cookies too, if you're extra, like me!