Make the Cookie Dough:
In a mixing bowl, cream the room temperature vegan butter, ½ cup white sugar, and brown sugar using an electric mixer for about 2 minutes until fluffy.
Add the flax egg and vanilla bean paste to the bowl. Mix for about 30 seconds until combined.
Add the flour, baking powder, pumpkin pie spice, and salt to the bowl. Start mixing until a thick dough forms. The dough will start off crumbly but will soften as you mix.
Cover the bowl with plastic wrap and chill the dough in the fridge for 30 minutes to 1 hour (or up to 24 hours).
Make the Pumpkin Pie Filling:
While the dough chills, mix the pumpkin puree, maple syrup, oat milk, cornstarch, vanilla, and pumpkin pie spice in a bowl until smooth. Set aside.
Assemble & Bake the Cookies:
Preheat the oven to 350°F (180°C) and line a baking sheet with parchment paper.
Remove the dough from the fridge. Scoop out 10-11 evenly sized cookie dough balls using a cookie scoop. Roll each ball between your palms, then roll them in the reserved 2 tablespoons of sugar to coat.
Place the dough balls onto the baking sheet, flatten each slightly with your palm, and use your thumb to create an indent in the center of each cookie. Use your fingers to enlarge the indent slightly.
Spoon about 1.5 Tablespoons of the pumpkin pie filling into the center of each cookie, ensuring the filling stays within the cookie’s edges.
Arrange the cookies at least 2 inches apart and bake for 12-14 minutes, until the edges are crisp and the pumpkin filling starts to crinkle.
Let the cookies cool on the baking sheet for 5 minutes. Use a spoon to gently reshape the edges if necessary, then transfer to a wire rack to cool completely.
Serve:
Once cooled, top each cookie with a dollop of vegan whipped cream and a sprinkle of pumpkin pie spice. Serve and enjoy!