Preheat the oven to 350 degrees F. Line 2 baking sheets with parchment paper.
Place the butter and sugars in a stand mixer fitted with a paddle attachment. Beat until fluffy, about 2 minutes. Add the wine, cranberry juice and orange zest. Beat until combined; it's okay if the mixture looks slightly curdled.
Whisk together the flour, baking powder, Chinese five-spice and salt in a large bowl. Pour half of the dry ingredients into the butter mixture and beat on low speed until combined. Repeat with the remaining dry ingredients until a loose dough comes together. Add in the food coloring and beat just until homogenous, scraping down the sides of the bowl as needed.
Using a 3/4-ounce scoop, make small mounds of dough on the prepared baking sheets, leaving about 2 inches of space between each cookie. Sprinkle the tops of the cookies with the crushed cranberries. Bake until the cookie tops are dry and slightly wrinkled, 12 to 14 minutes.
When measuring flour, we spoon it into a dry measuring cup and level off excess. (Scooping directly from the bag compacts the flour, resulting in dry baked goods.)