InstructionsReset

1. Make the dough

   Place the almonds in a food processor. Pulse until the almonds are finely chopped, but not so finely that it’s turning into almond flour. See photo above for a visual.
2. In a medium bowl, whisk together the chopped almonds, flour, baking powder, cinnamon, and salt until combined. Set aside.
3. In a large bowl using a handheld or stand mixer fitted with a paddle attachment, beat the butter and sugar together on high speed until completely smooth and creamy, about 3 minutes. (Here’s a helpful tutorial if you need guidance on how to cream butter and sugar.) Add the egg, vanilla extract, and almond extract, and beat on high speed until combined, about 1 minute. Scrape down the sides and up the bottom of the bowl and beat again as needed to combine.
4. Add the dry ingredients to the wet ingredients and mix on low speed until combined. The dough will be thick and crumbly, and weigh about 850g.
5. Divide the dough into 2 equal portions (about 425g each, or just eyeball it), gently flatten into discs, and wrap each in plastic wrap. Chill the discs in the refrigerator for at least 3 hours (and up to 4 days).
6. Preheat oven to 350°F (180°C). Line baking sheets with parchment paper or silicone baking mats. (Always recommended for cookies.) Set aside.

7. Cut out and bake the cookies

   Remove 1 disc of chilled cookie dough from the refrigerator. After chilling, the dough will be very hard. Let it sit at room temperature for 10 minutes (or 30 minutes, if the dough chilled for longer than 3 hours) before you try to roll it. Generously flour a work surface, as well as your hands and the rolling pin. Roll out the disc to about 1/4-inch thickness. If the dough is cracking a lot when rolling out, wait a few more minutes for it to soften up a bit more. The more you work with it, the softer and easier to work with it will become. Using a 2-inch or 3-inch cookie cutter, cut dough into shapes. Re-roll the remaining dough and continue cutting until all is used. Repeat with the second disc of dough. You should have about 44–60 cookies, depending on the size of cookie cutter you use.
8. Using a small (1-inch) cookie cutter (see Note if you don’t have one), cut a hole into the center of half of the cookies. Let’s call these the “top cookies,” and the ones without a hole the “bottom cookies.”
9. Arrange the cookies 2 inches apart on lined baking sheets. Bake the cookies for about 11–12 minutes, or until lightly browned around the edges. Allow cookies to cool on the baking sheets for 5 minutes, then transfer to a wire rack to cool completely before assembling.

10. Make the icing:

    In a small bowl, whisk together (I usually use a fork) confectioners’ sugar, 1 Tablespoon milk, and extract(s) until smooth. If the icing is too thick to whisk, add a little more milk, a teaspoon at a time, until it reaches desired consistency. You want to keep it on the thicker side.
11. Lightly dip the surface of each top cookie into the icing, and let any excess icing drip off. Place the iced top cookies on a wire rack or parchment paper. It’s ok if the icing is not completely set before sandwiching the cookies.

12. Assemble the cookies

    Spread about 1/2 teaspoon of cherry preserves on the bottom side of each bottom cookie. Carefully top each bottom cookie with a top iced cookie and press together very gently to create a cookie sandwich. Icing will set in a few hours, so you can stack, store, transport, and gift the cookies.
13. Cookies will stay fresh covered at room temperature for 2 days or in the refrigerator for up to 1 week.