Preheat the oven to 325°F. Line baking sheets with parchment paper or silpat mats.
MAKE THE COOKIES:
Spread the cherries on paper towels to drain well. Chop finely; set aside.
In a large bowl, whisk together the flour and sugar. Using a pastry blender, cut in the butter until the mixture resembles fine crumbs. Stir in the chopped cherries and 4 ounces of the chopped chocolate. Stir in the almond extract and, if desired, food coloring. Knead the mixture with your hands until it forms a smooth ball.
Shape the dough into ¾-inch balls. Place the dough balls 2-inches apart on the prepared cookie sheets. Using the bottom of a drinking glass dipped in water and then sugar, flatten the dough balls to 1½-inch rounds.
Bake the cookies for 12 to 14 minutes or until the centers are set. Cool for 1 minute on the cookie sheet, then transfer the cookies to a wire rack and let cool completely.
DIP THE COOKIES:
Place the remaining chopped chocolate or disks + shortening in a glass bowl or measuring cup. Heat and stir in 30 second intervals in the microwave until melted and smooth (or melt in a small saucepan over low heat on the stove). Dip half of each cookie into the melted chocolate, allowing excess to drip off. Place cookies on waxed paper until the chocolate is set.
Notes
*To store: Layer cookies between waxed paper in an airtight container; cover. Store at room temperature for up to 3 days or freeze for up to 3 months.