In a large mixing bowl, whisk together the sifted powdered sugar, 5 tablespoons of whole milk, light corn syrup, alcohol-free vanilla flavoring, and a pinch of salt until the mixture is smooth and lump-free.
Perform the 'ribbon test' by lifting the whisk and letting the icing drizzle back into the bowl; for a general-purpose consistency, the trail should disappear back into the base within 8 to 10 seconds.
To create 'Outline Icing' for borders, add more powdered sugar one teaspoon at a time until the icing is thick enough that the ribbon takes about 15 seconds to merge.
To create 'Flood Icing' for filling the centers, add additional milk half a teaspoon at a time until the icing is thin enough that the ribbon merges back instantly (within 3 to 4 seconds).
Divide the icing into separate small bowls if using multiple colors, and stir in gel food coloring with a toothpick until your desired shade is achieved.
Transfer the icing to piping bags fitted with small round tips or into plastic squeeze bottles for better control.
Pipe the borders of the cookies first using the thicker outline icing and let them set for 5 minutes before filling the centers with the thinner flood icing.
Use a toothpick to pop any small air bubbles that appear on the surface while the icing is still wet.
Allow the decorated cookies to dry at room temperature for at least 4 hours to set the surface, or up to 24 hours if you intend to stack them in containers.