In the bowl of a stand mixer fitted with the paddle attachment, add the flour, cocoa powder, sugar, anise seeds, and salt. Mix to combine.
Scatter the butter over the top of the flour mixture. Turn the mixer to low and mix until the butter becomes the size of small peas. Stream in the cold water and almond extract and mix until just combined. Turn the dough to a lightly floured work surface and form the dough into a disk that’s about 1 inch thick. Cover with plastic wrap and refrigerate for 1 hour.
Preheat the oven to 350°F. Line three baking sheets with parchment paper (or silpat). On a floured work surface, roll out the disk of dough to ¼” thickness. Using a 2-inch round cookie cutter (or a shot glass) cut out rounds and place 1 inch apart on the baking sheet. Repeat with the other disk, and re-roll the scraps of the dough until you get 60 cookie rounds.
Sprinkle the tops of the cookies with the decorating sugar. Bake the cookies for 15-20 minutes, or until they’ve puffed up and are dry to the touch, rotating the pans halfway through. Transfer the cookies to a wire rack to cool completely.
Pour the heavy cream in a small saucepan and place over medium-low heat on a stove. Bring to a boil and then immediately pour over the dark chocolate. Let the mixture sit for 1 minute.
Using a whisk, start to gently whisk the cream and the chocolate, starting at the center, and working your way outwards. Once smooth, add the butter, vanilla, and liqueur. Once combined, add the raspberry preserves. Place a sheet of plastic wrap over the ganache and gently press it the surface so the ganache doesn’t form a skin. Place the bowl in the fridge to set.
Once the ganache comes to a pipeable consistency, place it in a piping bag. Cut the bag to form a small opening and pipe approximately 1 teaspoon of the ganache on one side of a cookie round. Gently sandwich together. Repeat until you have 30 sandwich cookies. Let sit until the ganache sets, then serve.
Tools: parchment paper, piping bag, 3 baking pans, spatula, whisk
These cookies can be kept at room temperature in an airtight container for up to 3 days.
Recipe provided by Bob's Red Mill