- ½ c butter, softened but not melted
- ½ c brown sugar
- ½ tsp salt
- 1 tsp vanilla
- 1 to 2 tbsp milk (so mixture can be easily rolled into balls)
- 1-½ c Gold Medal flour
- powdered sugar (to coat cooled cookies)
- ½ c DARK chocolate chips
- 1 tbsp shortening
- 2 tbsp light corn syrup
- 1 tbsp water
- 1 tsp cherry juice (from Maraschino cherry jar)
- 30 maraschino cherries (stems removed and well drained)
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. (Add additional 1 tbsp milk if needed.)
Using a spoon or a 1-¼" cookie scoop, put dough into palm of hand and roll between palms to form 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 -- NOT maraschino cherries) to a microwave-safe dish. Micro on high for 20 seconds. Stir and micro again another 10 seconds. Mix chocolate until silky smooth. Return to micro 5 seconds at a time if necessary.
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.
Make ahead tip: Make cookies and freeze or store in air-tight container until needed. Mix chocolate filling just before serving. Top with cherry and serve.