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A silver platter piled with Jack-o-Lantern shaped sandwich cookies featuring jack-o’-lantern faces.
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Jack-o'-Lantern Cookies

Chocolate-filled spice cookies are even more fun with jack-o'-lantern faces!
Prep Time40 minutes
Cook Time10 minutes
Chilling Time1 hour
Total Time1 hour 50 minutes
Course: Cookies
Cuisine: American
Keyword: chocolate ganache sandwich cookies, Halloween sandwich cookies, jack-o’-lantern sandwich cookies
Servings: 18 Sandwich Cookies

Ingredients

For the Cookies

For the Chocolate Ganache

Instructions

  • In a large mixing bowl, beat the butter, brown sugar and granulated sugar until light and fluffy.
  • Beat in the eggs one at a time, then mix in the vanilla extract.
  • In a separate bowl, whisk together the flour, cornstarch, baking soda, salt, cinnamon, ginger and allspice.
  • Gradually add the dry ingredients to the butter mixture, mixing just until a soft dough forms.
  • Divide the dough in half and shape each portion into a disk. Wrap tightly and refrigerate for at least 1 hour.
  • Preheat the oven to 350°F. Line baking sheets with parchment paper.
  • On a lightly floured surface, roll the dough to about ¼-inch thickness.
  • Cut out 36 pumpkin-shaped cookies. Using a small sharp knife or mini cutters, cut jack-o'-lantern faces into half of the cookies.
  • Space the cookies about 2 inches apart on the prepared baking sheets and bake for 8 to 10 minutes.
  • They're done when the edges are lightly golden and the centers are set. They firm up more during cooling, so don't bake until hard.
  • Allow the cookies to cool on the baking sheets for 5 minutes before transferring them to a wire rack to cool completely.
  • Add the chocolate chips to a heat-safe bowl and add the cream. Heat in the microwave for 40 seconds.
  • If the chocolate chips aren't melted and smooth, reheat for additional 10 seconds increments until they are.
  • Remove the ganache from the microwave and stir well. Allow it to cool until it thickens to a spreadable consistency.
  • Pipe or spread a large tablespoon of ganache onto each solid pumpkin cookie, leaving a small border around the edge.
  • Place a jack-o'-lantern cookie on top and gently press until the filling reaches the edges.
  • Allow the ganache to set for about 30 minutes before serving.

Notes

Give the faces some space: I've experimented with different designs and found that cutting narrow teeth or leaving tiny strips of dough between the openings is very tricky! Those delicate pieces are harder to transfer without breaking.
Go lightly with the flour: Dust the rolling surface just enough to stop the dough sticking. Working lots of extra flour into the dough can make your cookies dry.
Wait before filling: Both the cookies and ganache need to cool before you assemble the jack-o'-lantern cookies. Warm cookies or runny ganache can leave you with chocolate leaking through the faces. That might look scary but not in a good way!

Nutrition

Calories: 393kcal | Carbohydrates: 44g | Protein: 5g | Fat: 22g | Saturated Fat: 14g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 6g | Trans Fat: 1g | Cholesterol: 67mg | Sodium: 141mg | Potassium: 125mg | Fiber: 2g | Sugar: 19g | Vitamin A: 602IU | Vitamin C: 0.1mg | Calcium: 34mg | Iron: 2mg

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