Spray 2 (24 cups each) mini muffin pans with cooking spray.

Grind the candy canes in the food processor until very finely ground. Remove from the food processor and set aside.

Put 1 cup butter and the cream cheese in the food processor and process until smooth. Add the flour, cocoa powder, ½ cup sugar, 1 tablespoon vanilla, and ¼ teaspoon salt. Process to combine. Add ½ cup of the ground candy canes and process to combine. Divide the dough into 48 balls. Place 1 ball in each muffin tin and refrigerate for 1 hour.

Preheat oven to 325 degrees.

Using your thumb or the end of a French rolling pin, press a hole into the center of each ball of dough.

Whisk together the 2 tablespoons reserved maraschino cherry juice with 1 tablespoon melted butter, ½ cup sugar, ¼ teaspoon salt, the egg, and 1 teaspoon vanilla. Spoon the mixture into each hole.

Pat the cherries dry with paper towels and place one in each hole on the filling. Sprinkle the cookies with the remaining crushed candy canes.

Bake for 25 minutes. Let cool in pan for 5 minutes then remove to a wire rack to finish cooling.