Make cookie dough according to the recipe. Divide dough into two disks and wrap each in plastic. Place in freezer for 20 minutes or until stiff. Remove one disk and place between sheets of parchment paper that have been dusted with flour. Roll out to 1/8" thick, dusting with more flour if dough begins to stick. Cut out vampire “heads” with 2" round cutter. Use a spatula to transfer to parchment-lined cookie sheet. Re-roll scraps and repeat with remaining dough. If dough gets too soft, refrigerate 10 minutes. (You will only need 12 cookies but make them all anyway. Trust us!)
Bake cookies 7–9 minutes just until firm in the center. Remove from oven and leave on pan for 2 minutes then transfer to rack to cool.
In a large bowl, combine powdered sugar and 2 Tbsp of milk. When smooth, add more milk until you reach glaze consistency.
Place rack with cooled cookies over parchment or plastic wrap. One at a time, dip entire top of each cookie into the glaze. Return to the rack and let excess drip off. When glaze has hardened, use the black frosting to make eyes and the widow’s peak hair. Use white or red frosting to make fangs.
Cut each strawberry fruit roll up into four pieces (like you would cut a pie). Lay each triangle with the point aimed at you. Put a dab of frosting opposite the point to help anchor the cookie. Place the vampire head on the dab of frosting and press to secure. Loosely wrap the roll-up around the head and squeeze the bottom tightly to hold in place. Repeat with remaining cookies.
No black icing on-hand? No problem! You can find it in the baking section at your local supermarket.