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A few simple tips can improve the quality of your cut-out cookies and make the process of holiday baking more enjoyable:
Refrigerate your dough first (30–60 minutes) and put your cookie cutters in the freezer for a few minutes before you're ready to use them.
Roll your dough in small chunks directly on silicon mat or piece of parchment paper that can go into the oven on the baking sheet. (That way you won't have to pull delicate cookies off the tray with a spatula when they're done. You can just lift the whole thing onto a cooking rack.)
Roll out your dough evenly at the right thickness. Most dough works best at 1/8 inch to 1/4 inch. You can buy spacers for you rolling pin that will help you get the dough to a certain thickness, but you can also use regular rubber bands. Just put them on either end of the rolling pin to leave that much room between the pin and the surface you're rolling on.
If your dough will expand a lot in the oven and you're using detailed shapes, roll thinner. If your dough doesn't expand much and/or you're using shapes without much detail, roll thicker.
Be careful with thin dough. If you roll dough too thin, the cookies will burn and be brittle and break easily when you take them out of the oven.
Use cutters with softer corners with expanding dough. Dough generally expands outward as well as upward, so it doesn't keep exactly the same shape as it cooks.
Large, thick cookies need to bake longer at a lower temperature than other cookies so they aren't doughy in the middle and burnt on the edges.
For angels, gingerbread men, and other shapes that need all their limbs intact, dip cookie cutters in flour or oil before using.
Place your cutter and press straight down (don't wiggle or twist). If you have your dough on the surface it will bake on, you can just remove the excess and leave the cookies where they are. If not, use a thin metal spatula to move cookies to the baking sheet.
After you've cut out your cookies and put them on the tray, refrigerate the whole tray for about 10 minutes. This will help keep your cookies the same shape they should be.
A note about washing and storing your cookie cutters: