Preheat oven to 375.
Cream together butter and sugar and vanilla
Mix in flour (your dough will look crumbly).
Roll dough into round balls or use a cookie scoop and place on a parchment-paper lined cookie sheet.
Make thumbprints in each dough ball and fill with a cherry from the pie filling.
If the dough is even a little bit warm (or “room temperature”), place your cookie sheet in the freezer for 15 minutes to allow the dough to chill back up. You want to put these cookies in the oven while the dough is still cold to minimize spreading!
Bake for 15 mins until edges start to get lightly brown and cookie sets up.
Allow to cool on cookie sheet for 15 minuutes.
Mix powdered sugar with milk to make a thick glaze
Pour icing in to a piping bag outfitted with a fine tip
Pipe icing in perpendicular lines across cookie to decorate.