In your stand mixer, blend the butter, sugar, and egg with the whisk attachment until smooth and creamy. Add the vanilla and mix again.
In a separate bowl, mix the flour and salt, then slowly add that into the wet mixture until the dough is nice and smooth.
Roll out half of the dough on a floured piece of parchment paper until it’s about ½ inch thick. Use a 3-inch round cookie cutter to make circles, then cut each circle in half to create little watermelon slice shapes.
Place them on a parchment-lined baking sheet.
Bake at 350°F for 10–12 minutes, or until the edges just start turning golden. Let them cool completely on a wire rack before decorating.
In your mixer, whisk together the warm water, meringue powder, and Karo syrup until smooth. Slowly add the powdered sugar (a couple cups at a time), mixing on low speed until everything’s blended and creamy.
Now split your icing into four bowls. One gets 2 tsp of watermelon Jello powder + a couple drops of hot pink food coloring. The others get lime green, dark green, and black food coloring—one color per bowl.
Decorate the Cookies. On the rounded edge, pipe a thick line of lime green on the outside, then a second line just inside that.
Outline the pink part of the “watermelon” and fill it in with the hot pink icing.
Between those two green lines, add a skinny strip of dark green. Add little black dots on the pink part and use a cookie scribe or toothpick to drag them down slightly—they’ll look just like seeds!
Let the icing set for at least an hour before serving or packaging them up.