Begin by preheating your oven to 350°F. Combine 1 tablespoon flour with 1/2 tablespoon cocoa, then use this mixture to grease and dust two 9-inch cake pans—this prevents sticking and adds subtle chocolate flavor to the edges. In a separate bowl, sift together 2 cups flour, 3/4 teaspoon salt, and 2 teaspoons baking powder, then set aside. Drain the 4-ounce bottle of maraschino cherries, chop them, and reserve both the cherries and their juice for later use.
In a large mixing bowl, cream together 1/2 cup butter and gradually add 1 1/2 cups sugar, beating until the mixture becomes light and fluffy. Add 2 eggs one at a time, followed by 4 ounces of melted unsweetened chocolate and 1 1/3 cups evaporated milk, beating until the mixture is smooth. Gently blend in the sifted flour mixture, then fold in the chopped cherries along with their reserved juice, stirring until just combined. Divide the batter evenly between the prepared pans and bake for 25-30 minutes until a toothpick inserted in the center comes out clean.
Allow the cakes to set in the pans for 5-8 minutes before carefully removing them and transferring to cooling racks. Once completely cooled, split each cake layer in two to create four layers total. Prepare the frosting by whipping 2 cups of cold heavy cream until stiff peaks form, then fold in 1/4 cup Quik chocolate milk mix and 1/4 confectioners' sugar along with 1 teaspoon pure vanilla extract. Layer the cake halves with the chocolate whipped cream frosting between each layer and on top, garnishing with milk chocolate kisses if desired.
