Preheat oven to 375º.
Line two cookie sheets with parchment paper.
Cream shortening and sugar together, using a stand mixer if available.
You can also do it by hand.
Add molasses and vanilla and beat well.
Add pumpkin puree and whip until incorporated (don’t worry if the fat doesn’t mix in completely).
In a separate bowl, combine all the remaining ingredients and mix well.
Add this dry mix to the wet until all incorporated.
It will make a stiff batter.
If available, use ice cream scoop that has a release lever to drop the dough onto your cookie sheet.
Wet your fingers and gently flatten the dough balls.
This will prevent your pies from tipping over by creating a semi-flat surface for them to rest on.
Bake for 10-13 minutes or until a toothpick inserted comes out clean, and the tops spring back when pressed in the center.
Remove cookies from the cookie sheet as soon as they come out of the oven to prevent over-baking.
Cover them with a towel or plastic wrap to keep moisture/steam in, as this will prevent a hard crust from forming.
Prepare the filling while your cookies are cooling.
Whip the filling ingredients together until smooth.
Set aside or refrigerate until use.
Use a pourer to pour the filling into the center.
Make sure the sides of the cookies that were touching the cookie sheet are the side that touch the filling.
Optionally, you can mix in mini chocolate chips or some melted chocolate drizzled over the top.
Store them wrapped in plastic wrap or in an air-tight container to keep them soft.