Directions

Makes about 20 cookies using 2½-inch cutters.

Note for sandwich cookies: Roll the dough to approximately 3/16-inch thickness (between ⅛ and ¼ inch) and bake for 10–11 minutes. To check for doneness, carefully lift and turn over a cookie with a spatula. The bottom should be medium golden brown.

1. Add the butter, sugar, and vanilla to a mixing bowl. Cream together using the back of a tablespoon (a dinnerware spoon) until smooth and well combined.

2. Whisk together the dry ingredients in a separate bowl. Add half to the butter mixture and mix thoroughly using the back of the spoon. Add the remaining dry ingredients and mix until combined.

3. Press the dough together, knead 3–4 times in your hands, and divide into two pieces.

4. Cut a piece of plastic wrap large enough to fold over the dough. Place one piece of dough on one half of the wrap, fold the other half over it, and roll to approximately ¼-inch thickness. Rolling between the layers of plastic wrap prevents the dough from sticking to the rolling pin.

5. Fold the edges of the plastic wrap around the dough and refrigerate until firm, about 1 hour. Repeat with the remaining dough. This rest allows the gluten to relax for a more tender cookie.

6. Remove the dough from the refrigerator and unwrap it. Cut out pumpkin shapes or rounds and place them 1–2 inches apart on a baking sheet lined with parchment paper.

7. Gently press the scraps together, roll to the same thickness, and refrigerate until firm before cutting out additional cookies. Bake these separately if needed.

8. Place the baking sheet in the refrigerator while the oven preheats. Position a rack in the center of the oven and preheat to 350°F.

9. Remove the baking sheet from the refrigerator and bake the ¼-inch-thick cookies for 11–12 minutes. To check for doneness, carefully lift and turn over a cookie with a spatula. The bottom should be medium golden brown. The cookies will crisp as they cool.

10. Let the cookies cool on the baking sheet for 5–10 minutes, then transfer to a wire rack to cool completely.

11. Arrange the cooled cookies on parchment paper so they are ready to drizzle before melting the chocolate.

Chocolate Drizzle

1. Add about 1 inch of water to a small saucepan and bring to a gentle simmer.

2. Place the chocolate in a dry, heatproof bowl and set it over the saucepan. Make sure the bottom of the bowl does not touch the water and keep water out of the chocolate.

3. Heat until the chocolate has melted, stirring gently as needed. Remove the bowl from the saucepan and stir until smooth.

4. Transfer the melted chocolate to a squeeze bottle suitable for warm chocolate and immediately drizzle over the cookies. For extra flair, use the tip of the squeeze bottle to draw jack-o’-lantern faces.

Chocolate Ganache

Note: Ganache is an optional filling for sandwich cookies.

1. Place the chocolate in a heatproof bowl. If using chopped chocolate, chop it finely for even melting.

2. Heat the heavy cream in a small saucepan or in the microwave just until it begins to boil, then pour it over the chocolate.

3. Let stand undisturbed for 3–4 minutes to allow the chocolate to soften and melt. Gently whisk until smooth.

4. Let the ganache cool until thick enough to spread without running.

5. Spread ganache on the flat bottom of one cooled cookie, then top with a second cookie, placing its flat bottom against the filling.