In a stand mixer, cream softened butter with the brown sugar. Add salt, vanilla and 1 tbsp milk, and mix until well blended. Add flour and mix until mixture forms coarse crumbs that stick together.
Using a spoon or a 1-¼” cookie scoop, roll dough into a 1″ to 1-¼” ball. Place balls on ungreased cookie sheet.
With thumb, form deep indent in each cookie. Bake at 375° for 10-12 minutes until firm but not brown. Remove cookies from sheet to a cooling rack and cool completely.
When cookies are cool, roll them in powdered sugar to coat thoroughly.
Add filling ingredients (dark chocolate chips, shortening, corn syrup, water, and cherry juice) to a microwave-safe dish. Micro on high for 20 seconds. Stir and micro again another 10 seconds. Mix chocolate until silky smooth.
Using a pastry bag or small spoon, fill each cookie indent with a mound of melted chocolate. Allow chocolate to set a few minutes, then add well-drained maraschino cherry to top of each cookie. Serve immediately or refrigerate no more than 2 hours.
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