Lightly spoon 1 cup all-purpose flour into a measuring cup, and level with a knife. Combine the flour with 1/3 cup unsweetened cocoa powder, 1/2 tsp. baking soda, and 1/8 tsp. salt; set aside.
Place 1/3 cup vegetable shortening (such as Earth Balance) in a stand mixer and beat until the shortening is fluffy. I probably should have let it soften a bit ahead of time, since mine never quite reached the fluffy stage, so I recommend removing the shortening from the fridge a little before you plan to make the cookies.
Add 2/3 cup vegan sugar about 1 tablespoon at a time, and beat after each addition. Add 1 teaspoon vanilla extract and the equivalent of 1 egg white made with egg replacer (such as Ener-G); beat until combined. Add the flour mixture and stir to combine. I found it helpful to use my hands as well as a wooden spoon, kneading the batter together into a dough more than I was actually stirring it.
Turn the dough out onto a piece of wax paper and shape into a 6-inch log, then wrap in the wax paper and freeze for 2 hours - you want it to be very firm.
Slice the log into 24 (1/4-inch thick) cookies. Place the cookies on baking sheets coated with cooking spray, and bake at 350 degrees for 10 minutes. Remove from the pans and cool completely on a wire rack.
Once cool, make the frosting: combine 2 cups organic powdered sugar and 3 tablespoons plain soy milk (such as Silk) in a large bowl; stir with a whisk until smooth. Transfer to a zip-top plastic bag and seal, then snip a tiny hole in one corner of the bag. On each cookie, pipe 3 concentric circles. Starting at the center circle, pull a toothpick through the other circles at regular intervals so you have a "web."Each cookie is 110 calories. Happy early Halloween!
Cost:
vegetable shortening $3.49
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