Preheat oven to 350 degrees F. Line cookie sheet with parchment paper. Set aside.
Combine flour, baking powder, baking soda, salt and 1/2 cup sugar in a medium bowl. Stir to combine.
Combine 1 cup granulated sugar and 8 ounces cream cheese in large mixing bowl or stand mixer bowl. Use an electric mixer to combine ingredients using medium speed. Mix until fluffy.
In a small bowl combine butter and chocolate. Melt in microwave for about 30 to 60 seconds or until melted. Stir until smooth and allow to cool slightly.
Add chocolate mixture, red gel food colouring and vanilla to cream cheese mixture. Mix until combined.
Add flour mixture to cream cheese mixture slowly, in 2 to 3 batches. Use the mixer to combine ingredients after you add each batch of flour mixture.
Cover bowl and place in the fridge for 30 minutes if you want your cookies to hold their shape.
Remove from fridge and roll into small 1 inch balls. Press down with the palm of your hand or use a fork dipped in water to press the cookies down. Place in oven and bake for about 8 to 10 minutes.
Remove from oven and allow to cool.
In stand mixer combine confectioners sugar and 8 ounces of cream cheese and mix until fluffy.
Add milk and vanilla, mix again until combined.
Transfer to a piping bag with large tip.
Pipe frosting onto the top of cookies. Press 3 cookies into each stack.
Serve with a big old holiday loving smile!