To prepare the cookies:

1. Preheat the oven to 350 degrees and line two sheet pans with sheets of parchment paper. Combine the dry ingredients and set aside. In the bowl of a stand mixer, cream the butter and sugar until smooth and well combined, about 2-3 minutes. Add the egg and extract and cream until combined. Add the dry ingredients and stir on low just until combined. 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. Place shapes on a baking sheet and freeze briefly to firm up slightly, about 5 minutes. Once chilled, gently insert the lollipop sticks into the cookie by turning the cookie stick back and forth gently as you insert it into the cookie. Make sure 1/3 of the stick is inserted into the cookie, and use your fingers to patch up any dough cracks or places where the stick has broken through. Spread the cookies about 2” apart on the prepared baking sheet and bake in the preheated oven for 10-12 minutes. 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. 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. Spread or pipe the icing onto the cookie as desired. I like to pipe the border onto each cookie and then fill in with a food-safe brush or knife. Allow to rest and set up, and enjoy!