Preheat the oven to 350°F and line two baking sheets with parchment paper. Make sure the oven is fully heated before baking so the cookies cook evenly.
Drain the maraschino cherries well, pat them completely dry, then chop finely. Toss the chopped cherries with 2 tbsp flour to prevent them from sinking into the dough.
In a bowl, mix the remaining flour with the salt and set aside.
In a large bowl, beat the butter and powdered sugar until light, fluffy, and pale, about 2 to 3 minutes.
Mix in the cherry juice, almond extract, vanilla extract, and food coloring if using. The dough should turn a soft pink and smell lightly almond scented.
Gradually add the flour mixture, mixing just until combined. Gently fold in the floured cherries so they stay evenly distributed.
Scoop about 1 tbsp of dough and roll into balls. Lightly roll each ball in granulated sugar and place them 1½ to 2 inches apart on the prepared baking sheets.
Bake for 10 to 12 minutes, until the edges are set and just starting to turn golden. The centers should still look soft.
Remove the cookies from the oven and immediately press a Hershey’s Kiss into the center of each one. Slight cracking around the edges is normal.
Let the cookies cool on the baking sheets for about 10 minutes, then transfer to a cooling rack to set completely.