In advance: Make cookies. Prepare and roll out dough. Cut pumpkins: 1 with 2nd smallest cutter, 2 with 2nd largest cutter and 2 with largest cutter. Bake and cool cookies. Outline all cookies with Cookie Icing. Heat bottle according to directions. Flow in icing to cover. Let dry. Using buttercream, pipe tip 5 dot eyes, tip 3 outline stems, dot nose, cheeks and pupils, outline or outline and fill-in mouths and bead tongue. Add tip 44 teeth. Pipe leaves using tip 349 on small cookie, tip 352 on larger cookies.
Bake and cool cake. Lightly ice mouth area smooth. Using tip 3, outline pumpkin rib lines. Cover with tip 16 stars. Pipe tip 2A dot eyes (flatten and smooth with finger dipped in cornstarch). Pipe tip 5 dot pupils. Overpipe nose and cheeks with tip 16 stars. Pipe tip 3 outlines for stem; add tip 366 leaves. Position cookies.
*Combine Orange with Red-Red for orange shown on cake.
The star tip creates the most celebrated, easily accomplished decorations! The serrated edges of the star tip make ridges in the icing as you squeeze it out. Because fill in requires so much piping from the same bag, keep replenishing icing in bag.