Line a baking sheets with parchment paper. You'll need 1 to bake cookies and the other to freeze the cookie dough balls in the freezer.
In a bowl fit with a mixer, cream butter, brown sugar, and granulated sugar until light and fluffy; about 30 seconds to 1 minute.
Beat in egg yolk, vanilla extract, almond extract, and salt.
Carefully beat in flour, 1/2 cup at a time, mixing just until moistened.
Beat mixture until combined and dough comes together. You may need to use a spatula to turn the bottom crumbs into the dough then mix again just to combine.
Scoop 3/4 tablespoon dough and roll into a ball then place cookie on parchment lined baking sheet. Indent the cookie in the center with a teaspoon dipped in powdered sugar to prevent sticking. Repeat until done.
Freeze cookie dough thumbprints for at least 30 minutes.
Preheat oven to 375 degrees F. Transfer cookies to parchment lined baking sheet. Place frozen cookies on baking sheet; about 1 inch apart.
Fill each center of the cookie with 1 cherry. Bake for 12 minutes.
Remove cookies from oven and top with an additional 1-2 cherries. Bake an additional 2 minutes in oven.
To make the topping combine powdered confectioners' sugar and water in a small dish. Use a spoon to drizzle over the top of each cooled cookie. I like to place a piece of wax paper below a cooling rack then drizzle the icing over each cookie.