In a medium bowl, whisk together the flour, cornstarch, ground ginger, cinnamon, baking soda, kosher salt, cloves, allspice, and nutmeg until evenly combined.

In the bowl of a stand mixer fitted with the paddle attachment, beat the butter and dark brown sugar on medium speed until light and fluffy, about 2 to 3 minutes. While mixing, drizzle in the molasses and continue to mix well, scraping down the bowl as needed.

Add the egg and vanilla extract to the butter mixture and beat until fully incorporated.

Reduce the mixer speed to low and add the dry ingredients in three batches, mixing just until combined after each addition to avoid overworking the dough.

Turn the dough out onto a lightly floured surface. Divide into two disks, wrap each tightly in plastic wrap, and refrigerate until firm, about 1 to 2 hours.

Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper.

Working with one dough disk at a time, keep the other refrigerated. Flour your work surface generously and roll the dough out to an eighth-inch thickness. Use a 2- to 3-inch round or shaped cookie cutter to cut out cookies. For half of the cookies, cut out smaller shapes in the center to create a window. Place cookies 2 inches apart on prepared baking sheets. Save cut-out dough for re-rolling or bake small cookies.

Bake in the preheated oven until the cookies are set but still soft, about 10 to 12 minutes. Let cool on the baking sheets for 5 minutes before transferring to wire racks to cool completely.

In the mixer bowl with the paddle attachment, beat softened butter, orange zest, vanilla extract, and salt on medium speed until creamy and well combined.

Reduce speed to low and gradually add powdered sugar, mixing until just combined. Scrape down the bowl, then increase speed to medium-high and beat until fluffy, about 1 minute. Transfer the frosting to a piping bag with a small tip clipped off.

In a small bowl, whisk jellied cranberry sauce until smooth and loosened for easy spreading.

Pipe a 1/4-inch thick ring of frosting on the underside of each whole cookie. Fill the center with a thinner layer of frosting, then add cranberry sauce on top.

Place a cookie with a cut-out center on top to sandwich the filling, aligning flat undersides together. Repeat with all cookies.

Optionally, dust assembled sandwiches with powdered sugar before serving.