In a large mixing bowl or the bowl of a stand mixer, cream together the softened butter and granulated sugar on medium speed until light and fluffy, about 2-3 minutes.

Beat in the large egg and vanilla extract until well combined, scraping down the sides of the bowl as needed.

In a separate medium bowl, whisk together the all-purpose flour, baking powder, salt, and ground cinnamon (if using).

Gradually add the dry ingredients to the wet ingredients, mixing on low speed until just combined. Do not overmix. Stir in the orange zest and finely chopped dried cranberries until evenly distributed.

Divide the dough into two equal portions. Flatten each portion into a disc, wrap tightly in plastic wrap, and refrigerate for at least 30 minutes, or up to 2 hours, to allow it to firm up.

Preheat your oven to 375°F (190°C). Line two baking sheets with parchment paper.

On a lightly floured surface, roll out one disc of chilled dough to about 1/4 inch thickness. Use your favorite Christmas-themed cookie cutters to cut out shapes. Carefully transfer the cut-out cookies to the prepared baking sheets, leaving about 1 inch between them. Reroll scraps as needed.

Bake for 8-12 minutes, or until the edges are lightly golden. Baking time will vary depending on the size and thickness of your cookies. Allow cookies to cool on the baking sheets for 5 minutes before transferring them to a wire rack to cool completely.

While the cookies cool, prepare the glaze: In a small bowl, whisk together the sifted powdered sugar, milk (or orange juice), and vanilla (or orange) extract until smooth and drizzle-able. Add more liquid a teaspoon at a time if the glaze is too thick, or more powdered sugar if it's too thin.

Once the cookies are completely cool, drizzle or spread the glaze over them. Allow the glaze to set for about 15-30 minutes before serving or storing.