To prepare the cookies:

1. Preheat the oven to 350 degrees.
2. Combine the dry ingredients and set aside.
3. In the bowl of a stand mixer, cream the butter and sugar until smooth and well combined, about 2-3 minutes. Scrape the sides of the bowl as needed. Add the egg and extract and cream until combined. Add the dry ingredients and stir on low just until combined.
4. Dump the dough crumbles out on to a lightly floured surface and work together into one ball with your hands. Using a rolling pin, roll the dough to just over 1/4″ thicken and use a medium sized cookie cutter to cut shapes. If the dough ever gets too soft, refrigerate briefly.
5. Place shapes on a baking sheet and freeze briefly for about 5 minutes.
6. Once chilled, bake in the preheated oven for 10-11 minutes, or until the edges are set, and cool on a cooling rack. Allow cookies to cool completely prior to icing.

For the icing:

1. Sift or whisk powdered sugar to remove lumps.
2. Add 3 tablespoons of the milk and the extract, whisking until combined. Continue to add milk until it is the right viscosity. You will want thicker frosting for piping. To test viscosity, run your whisk or a knife through the bowl of frosting- your frosting should slowly move back together until you can’t see any trace of the whisk any longer. This process should take about 10 seconds. If the frosting is too thick, it will not pool back together, and if it is too thin, it will pool back together too quickly. The ten second test doesn’t lie. Add more milk for a thinner icing and more powdered sugar if your icing becomes too thin.
3. Cover tightly in a tupperware or with a wet paper towel if you are not using it immediately, as frosting will dry out and become clumpy. Whisk occasionally and add more milk if it becomes too thick.
4. Fill piping bag halfway with sugar cookie frosting. Pipe borders around cookies, being careful to not get too close to the edge. Using a paint brush, “paint” frosting into the center of the cookie, filling in to the outside border. (For a good tutorial on this method, check out the Ina Garten video here) I typically will border and fill 4-5 cookies at a time. Continue this process until all the cookies are iced. Set aside for 3 hours, or until icing is set and dry. If you’re in a humid climate, you can use a small fan pointed at the cookies to help expedite this process.

To splatter your cookies:

1. In a small bowl, mix together 1 tablespoon of the cocoa powder and the vanilla extract until a thin, watery slurry comes together.
2. Hold your paint brush or natural bristle pastry brush at the base of the bristles. Squeeze, applying a small amount of pressure with your fingers to fan the brush slightly. Dip the tips of the brush in the cocoa/vanilla “paint” and find a spare corner of your covered work space to practice your splatter. While continuing to fan your brush with one hand, use the fingers of your other hand to lightly pull back the bristles and release. This will be a slingshot type of movement and will result in a splatter effect on your work surface. Once you’re confident with your speckling skills, move on to the cookies! Splatter away and allow to dry before storing.