1. Preheat oven to 325 F degrees.
2. Line 2 baking sheets with parchment paper.
3. Using a standing mixer fitted with a paddle attachment, set on medium speed:  cream the butter for 1 minute until fluffy and light.  Add the sugar and mix for another minute until well mixed.
4. Add the vanilla and almond extracts and mix for 30 seconds more.
5. Scrape down the sides of the bowl and turn the mixer speed down to low and then — 
6. Slowly add the flour, 1/2 cup at a time.  Mix until a crumbly consistency forms; it doesn’t look like a ball at this stage.  Use a rubber spatula to scrape the sides of the bowl again.
7. With clean hands, take the crumbly dough out and mix by hand until a nice ball forms.  
8. Wrap tightly in plastic wrap and refrigerate for 2 hours (the longer the better so the cookies keep their thumbprint shape and do not flatten).
9. Remove the cookie dough from the refrigerator.  Working quickly while the dough is chilled, use a 1-tablespoon measuring spoon or cookie dough scoop, and scoop out 1 tablespoon of dough for each cookie.  With your hands, roll each scoop of dough into small 1 to 1-¼” balls.  These are not big, wide cookies.
10. Toss each ball in sugar to coat the cookie dough (in a plastic bag or small bowl). Optional.
11. Place each ball on the parchment paper-lined baking sheets, about 1 inch apart.
12. With your thumb, dipped first in powdered sugar (to prevent sticking to the dough), gently press down in the center of each ball of dough to make a deep thumbprint.  Work quickly so the cookie dough doesn’t melt and become too soft.  It’s OK if there are a few cracks.
13. Freeze the cookie dough balls while still on the parchment paper-lined baking sheets for 30 more minutes to an hour.
14. Bake for 15 – 20 minutes until set, but not golden brown, keeping a sharp eye on them at the end so that they don’t overbake.  Shortbread cookies aren’t hard, they are softer than most cookies.
15. Remove cookies from the oven and allow them to cool completely while still on the baking sheets, for another 20 – 30 minutes.  I always press lightly down into the thumbprint indentation while the cookies are still warm.
16. As mentioned in the list of ingredients, strain out all of the excess syrupy juice from the can of cherry pie filling.  Add a drop or two of almond extract to the strained cherries, GENTLY mixing so that the cherries don’t break apart.
17. Spoon 2 – 3 cherries in the indented thumbprint on top of each baked cookie, trying not to add very much of the syrupy juice (which will just spread all over the cookies).

Prepare the Icing:

1. While the cookies are baking and/or cooling:
2. Whisk the powdered sugar, milk, and vanilla (and optional drops of lemon juice) together until smooth in a small mixing bowl.
3. Pour the icing into a small sandwich-size plastic storage bag.  Snip a very, very tiny hole in one of the bottom corners of the plastic bag.  
4. Slowly drizzle the icing over the cookies.
5. Enjoy!!