How to get round sugar cookies to stay round when you transfer them to the pan:
Start with a larger size circle than the finished cookie. Transfer the cookie to the baking sheet. Use the smaller cutter to cut out the correct size circle. Peel away the wonky edge, and you have a round cookie!

Less mess (and less flour) rolling method:
Roll the dough out between two pieces of plastic wrap. It takes a little getting used to, but you don’t end up with tough, over-floured cookies. 🙂

Stenciling on Cookies
What I Learned: When stenciling white on a cookie, add some white food color to the freshly made royal icing. If not, I get the pleasure of hand painting all the wheels with white Poppy Paint once the royal icing absorbs butter from the cookies. – You can see what I mean on my Cassette Tape cookies. 🙂