Chocolate Gingerbread Sandwich Cookies

Step 1

Whisk the flour, baking soda, salt, ginger, cinnamon, allspice, and cloves together in a large bowl. Set aside.

Step 2

In a large bowl using a hand-held mixer or stand mixer fitted with a paddle attachment, beat the butter and brown sugar together on medium speed until combined and creamy, about 2 minutes. Add the molasses and beat on medium speed until combined. Scrape down the sides and bottom of the bowl as needed. Beat in egg and vanilla on high speed for 2 full minutes. Scrape down the sides and bottom of the bowl as needed. The butter may separate– that’s ok.

Step 3

On low speed, slowly mix the dry ingredients into wet ingredients until combined. The cookie dough will be quite thick and slightly sticky. Divide dough in half and place each onto a large piece of plastic wrap. Flatten into a 1-inch disc and wrap each up tightly. Chill discs for at least 3 hours and up to 3 days. Chilling is mandatory for this cookie dough. I always chill mine overnight. If chilling for longer than 3 hours, allow to sit at room temperature for at least 20 minutes before rolling because the dough will be quite hard.

Step 4

Preheat oven to 350°F (180°C). Line baking sheets with parchment paper or silicone baking mats.

Step 5

Remove 1 disc of chilled cookie dough from the refrigerator. Generously flour a work surface, as well as your hands and the rolling pin. The dough may become sticky as you work, so keep extra flour nearby to use as needed. Alternatively, the dough may crack when rolling out. Wait a few minutes for it to soften back up. The more you work with it, the softer (and easier to work with) it will become. Roll out the disc until 1/4 inch thick. Using a 2.5-inch round or fluted cookie cutter, cut dough into circles. Re-roll the remaining dough and continue cutting until all is used. Repeat with the second disc of dough. You should have about 60 circles.

Step 6

Using a smaller cookie cutter or 1-inch fluted cookie cutter, cut a hole into the center of half of the circles. Let’s call these the “donut cookies” because of that center hole.

Step 7

Arrange the whole circles and the donut cookies 2 inches apart and on separate baking sheets (because the donut cookies take 1 less minute to bake).

Step 8

Bake the whole circles for about 12-14 minutes, or until set around the edges, and bake the donut cookies for about 11 minutes. Rotate the baking sheets halfway through the bake time. Allow cookies to cool on the baking sheets for 5 minutes, then transfer all of the cookies to a wire rack to cool completely before assembling.

Step 9

Once cool, dust the “donut cookies” with confectioners’ sugar.

Step 10

Heat the cream in a small saucepan over medium heat until it begins to gently simmer. (Do not let it come to a rapid boil– that’s too hot!) Pour over chocolate chips, then let it sit for 2-3 minutes to gently soften the chocolate. Very slowly stir until completely combined and chocolate has melted. If it’s not melting, do not microwave it. Just continue to stir until smooth. Cool ganache for 10 minutes before using on the cookies. Ganache thickens as it cools and sets after a few hours.

Step 11

Spoon 1 teaspoon of ganache on the underside of each whole cookie. Carefully top each with a donut cookie and press down gently to create a cookie sandwich.

Step 12

Cookies stay fresh covered at room temperature for 2 days or in the refrigerator for up to 1 week.