In a large bowl or stand mixer, combine softened butter, granulated sugar, brown sugar, and salt. Beat together with a paddle attachment until thick and creamy. Scrape down the bowl so it’s evenly incorporated.

Add egg yolk, cinnamon, vanilla, and mix together well until smooth and creamy.

Sift flour into the egg and butter mixture and fold together until a soft dough forms. It’ll be crumbly at first before it starts to come together.

Line a baking sheet with parchment paper. Scoop the dough into 1 ½ tablespoon balls and place onto the parchment paper. Press an indent into the middle of each ball with your thumb.

Press the sides of the cookies with your fingers to form walls to hold the filling in.

Place the baking sheet into the freezer to chill while you preheat the oven to 355°F (180°C) and get started on the filling.

Combine brown sugar and egg in a medium bowl. Whisk together.

Add pumpkin purée, cornstarch, salt, pumpkin spice, and evaporated milk into the egg mixture. Whisk to combine.

Take the shaped cookie dough out of the freezer. Space out the cookie dough so there is about 2 inches of space around each cookie so they can spread in the oven. You can bake these cookies in a few batches.

Add 1 to 2 teaspoons of pumpkin pie filling into the middle of each cookie. Bake for 12-14 minutes or until the bottoms are lightly golden brown. Let them cool for one minute on the baking sheet before using a spatula to carefully transfer them onto a cooling rack to cool completely. Bake the rest of the cookies.

Pro Tip: Pop your bowl and whisk attachment into the freezer 5 minutes before getting started for a very thick whipped cream.

Add the cold cream, vanilla extract, and powdered sugar into a large bowl or stand mixer. Whip the mixture with a wire whisk attachment until stiff peaks form. It’s ready when it’s thick, creamy, and holds its shape. Transfer into a piping bag with a star tip (I used a Wilton 1M).

Pipe a dollop of whipped cream on each cookie right before serving! Sprinkle a bit of cinnamon or pumpkin spice mix on each cookie.