1/4cupcanned solid pack pumpkinnot pumpkin pie filling*
Preheat oven to 350 degrees and line cookie sheets with parchment paper or silicone baking mat.
In a medium bowl, whisk together flour, cocoa powder, baking powder, baking soda, and salt; set aside.
Use a mixer to beat shortening, sugar, and egg in a large bowl. Mix on high speed until smooth, about 3 minutes.
Slowly add half the flour mixture, then the milk and vanilla. Mix in remaining flour mixture.
Drop about 2 teaspoons dough onto prepared sheets, spacing 2 inches apart. Bake until cookies spring back when lightly touched, 10 to 15 minutes.
Transfer baking sheets to wire racks and let cool 10 minutes. Remove cookies from baking sheets and transfer to wire racks using a spatula; let cool completely.
Use mixer to beat softened cream cheese, softened butter, and confectioners’ sugar on medium speed until smooth, about 3 minutes. Add pumpkin, cinnamon, and nutmeg; whip until smooth, scraping down the bowl as necessary.
Pipe or spoon about 2 teaspoons filling on the flat sides of half the cookies. Sandwich with remaining cookies, keeping the flat sides down.
This recipe makes 46 small cookies, so 23 whoopie pies. If you prefer them larger, simply bake the same and increase the time by a minute or so if needed.
Be sure your cream cheese has been softened so you don't end up with any little bits of cream cheese in your filling.