In your food processor, pulse the flour, powdered sugar, salt, nutmeg and cloves until combined.With the processor running, drop in the pieces of butter, one at at time, pulsing a few times until the butter is evenly distributed, and the dough is moistened and crumbly.Add the dried cranberries, pecans and candied orange peel. Drizzle with the vanilla and milk, then process until the dough starts to stick together.Note: If you don't have a food processor, you can make the dough in a bowl with a pastry cutter to cut in the butter, then use your hands to work in the liquid. Using a food processor will chop the nuts and dried fruit more finely, as well, so if you want larger chunks in your cookies, you should finish the dough by hand.
Dump the dough out onto a clean counter and use your hands to finish bringing the dough together, kneading in any stray bits of flour. The dough should be soft, smooth and supple.
Shape the dough into a flat disk, wrap in plastic wrap, and refrigerate for 20 minutes.Prepare two baking sheets by lining them with sheets of parchment paper.
On a lightly floured surface, place the disk of dough, and dust the top of the dough with flour, too. Roll out to an even thickness of 1/4 inch thick.Use any size/shape cookie cutters to cut as many cookies as you can, placing the cut cookies 1-2 inches apart on the parchment lined baking sheets. Using a 2 1/2 inch cookie cutter, you'll get about 32 cookies from this recipe.Gather up the scraps of dough, roll them out again, and continue cutting as many cookies as you can.
Place the baking sheets with the cut cookies in the refrigerator and chill for 1 hour. Chilling the cut cookies helps to ensure they don't spread and hold their shape perfectly while baking.
Preheat the oven to 350F.Bake the chilled cookies on the center oven rack for about 11 1/2 – 12 minutes. The tops should be a very pale golden with no dark browning, and you should see tiny flaky layers around the edges. If you (very carefully) turn a cookie over with a spatula, the bottom should have light golden browning, with no appearance of raw or wet dough.
Cool the cookies for 5 minutes on the pan, then very gently transfer them to a cooling rack to cool completely. Shortbread cookies are delicate when warm, so handle with care.
In a bowl, whisk together the powdered sugar and orange juice until smooth and drizzly. You can dip one half of the cookies in the icing, scraping the excess off the bottom, or just use a spoon to drizzle or spread it on top of the cookies. Set the iced cookies on a cooling rack placed over a baking sheet to catch the drips.
After icing the cookies, wait 30-60 seconds, then sprinkle with the chopped fruit and nuts, before the icing sets. The icing will dry to the touch in a few minutes, but won't fully set for a few hours.