Preheat oven to 350°F (180°C). Using a permanent marker, draw 36 (4×1-inch) rectangles, evenly spaced, on 3 sheets of parchment paper (12 per parchment). Turn parchment over, and place on 3 baking sheets.
In the bowl of a stand mixer fitted with the paddle attachment, beat butter, confectioners’ sugar, orange zest, cinnamon, ginger, cloves, salt, nutmeg, allspice, and pepper at medium speed until well combined and creamy, 2 to 3 minutes, stopping to scrape sides of bowl.
In a medium bowl, sift together flour and cornstarch. With mixer on low speed, gradually add flour mixture to butter mixture, beating until combined.
Place about 1 cup (247 grams) dough into a piping bag fitted with a medium open star tip (Wilton 4B); pipe small dots of batter under parchment to adhere to baking sheets. Using drawn rectangles as guides, pipe batter in a zigzag pattern. (Dough will take some effort to pipe.) Repeat with remaining dough. Refrigerate for 15 minutes.
Bake until lightly golden and firm to the touch, about 14 minutes, rotating pans halfway through baking. Let cool on pans for 5 minutes. Carefully remove from pans, and let cool completely on wire racks.
Spoon Cherry-Port Buttercream into a large piping bag fitted with a medium open star tip (Wilton 4B); pipe about 2 tablespoons (30 grams) buttercream onto flat side of half of cookies. Place remaining cookies, flat side down, on top of buttercream. Serve immediately.