First, make the cupcakes. Preheat the oven to 350F, and prepare about 16 cupcake lines in a pan.
In a large bowl, mix together the pumpkin puree, vegetable oil, brown sugar, and milk.
Add in the flour, baking powder, baking soda, salt, pumpkin spice, and vanilla. Mix to combine.
Fill each cupcake liner about ⅔ of the way full. You should get 16-18 cupcakes.
Bake in preheated oven for 20 minutes, until a toothpick inserted in the center comes out clean.
Let cupcakes cool completely before frosting.
When ready, prepare the frosting.
Place the vegan shortening and vegan butter in the bowl of a stand mixer, and beat together until smooth and creamy. Add in the cocoa powder, vanilla, and salt, and mix to combine.
Mix in the powdered sugar, about 1 cup at a time, until a thick frosting forms. It is normal to need a bit of milk to get the consistency just right. Add in a few drops of black food coloring. Remember that the frosting WILL get darker as it sits, too.
To create the double decker frosting effect, first pour your sprinkles into a small shallow bowl.
Spread a layer of frosting onto your cupcakes, then dunk the top of the cupcake into the prepared bowl of sprinkles. You may have to roll it around a bit to get it all covered. Repeat with all cupcakes.
For the second portion, place the remaining frosting in a piping bag fitted with a 1M tip, and pipe a swirl of frosting on top of each cupcake. Top with a Halloween candy or edible decoration if desired.