In a large mixing bowl, whisk together the all-purpose flour, baking powder, and salt until combined. In another bowl, cream the unsalted butter and granulated sugar using a hand mixer until smooth and fluffy. Incorporate the egg yolk, vanilla extract, almond extract, and orange gel food coloring into the butter mixture. Gradually add the flour mixture and milk, mixing until a soft dough forms, making sure everything is well blended.

Once your Candy Corn Sugar Cookie dough is ready, divide it into two equal balls. Wrap each ball tightly in plastic wrap and place them in the refrigerator. Chill the dough for about 1 hour until it's firm enough to roll out easily.

After the dough has chilled, remove it from the refrigerator and let it sit for a few minutes. Roll out one ball between two sheets of plastic wrap to a thickness of ¼ inch. Using a sharp knife or cookie cutter, cut the rolled dough into triangle shapes that resemble candy corn. Carefully transfer the cut shapes to lined baking sheets, ensuring they are spaced about 2 inches apart for even baking.

Preheat your oven to 375°F (190°C). Once the cookies are shaped and on the baking sheets, bake them in the preheated oven for 9-11 minutes. Remove them from the oven and allow the cookies to cool completely on a wire rack before decorating.

While the cookies cool, prepare the chocolate coating. Melt the dark chocolate chips and shortening in a microwave-safe bowl, stirring every 30 seconds until smooth. Repeat the process for the white chocolate chips in a separate bowl. Once cooled, dip one end of each cookie into the dark chocolate, and then the other end into the white chocolate, creating a lovely candy corn effect. Let the decorated cookies set on a sheet of parchment paper.