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Cook on a Whim: Chocolate Ganache-Filled Jack-o’-Lantern Cookies

Cook on a Whim: Chocolate Ganache-Filled Jack-o'-Lantern Cookies - featured image

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Buttery, spiced pumpkin-shaped cookies filled with rich chocolate ganache and coated in cinnamon sugar, perfect for Halloween.

Ingredients

Scale
  • 3 sticks (1 1/2 cups) salted butter, softened
  • 1 1/4 cups light brown sugar, packed
  • 1 tablespoon pure vanilla extract
  • 2 eggs, at room temperature
  • 4 1/2 cups all-purpose flour
  • 1 teaspoon baking soda
  • 1 teaspoon cinnamon
  • 1/2 teaspoon ginger
  • 1/4 teaspoon nutmeg
  • 1/2 teaspoon salt
  • 2 cups chocolate chips (half milk, half bittersweet)
  • 1 cup heavy cream
  • 4 tablespoons salted butter
  • 1 cup cinnamon sugar

Instructions

  1. Place chocolate chips in a medium bowl.
  2. Heat heavy cream to just below a boil.
  3. Pour hot cream over chocolate chips.
  4. Let mixture sit for 3 minutes.
  5. Gently whisk chocolate until a thick, creamy, shiny ganache forms.
  6. Let ganache cool to room temperature and thicken slightly.
  7. In a large mixing bowl, cream together 1 1/2 cups softened butter, brown sugar, and vanilla for 3 to 5 minutes until light and fluffy.
  8. Add eggs, one at a time, and mix until evenly combined.
  9. Add flour, baking soda, cinnamon, ginger, nutmeg, and salt to the bowl.
  10. Beat until combined and the dough forms a ball.
  11. Generously flour your work surface.
  12. Divide the dough in half.
  13. Flatten each dough half into a disk.
  14. Roll out one dough disk to 1/4 inch thickness.
  15. Flour the top of the dough and dip your cookie cutter in flour.
  16. Cut out cookies using a pumpkin cookie cutter, ensuring an equal amount of solid and jack-o'-lantern shapes.
  17. Carefully transfer cut cookies to a parchment-lined baking sheet.
  18. Place the baking sheet in the freezer and freeze until cookies are firm, about 15 to 20 minutes.
  19. Roll out leftover dough scraps and repeat with the remaining dough disk.
  20. Preheat oven to 350 degrees F (175 degrees C).
  21. Bake cookies on the middle rack for 8 to 12 minutes, or until just lightly golden brown.
  22. Cool cookies on the baking sheet for 5 minutes.
  23. Transfer cookies to a wire cooling rack to cool completely.
  24. Melt 4 tablespoons butter in the microwave or on the stovetop.
  25. Brush the melted butter over the top half of the solid pumpkin cookies (the ones without faces).
  26. Sprinkle the buttered cookies with cinnamon sugar, or press them face down into a shallow dish of cinnamon sugar.
  27. Spread the room temperature ganache over the half of the cookies with no face (the solid pumpkin cookies).
  28. Place the top pumpkin-faced cookies over the chocolate ganache.
  29. Gently press to adhere the two cookie halves together.
  30. Serve cookies immediately or allow ganache to firm up before storing.

Notes

Ensure butter and eggs are at room temperature for the best dough consistency.
Do not overbake the cookies; they should be soft and chewy.
Use plenty of flour on your work surface and cookie cutter to prevent sticking.
Freezing the cut-out cookies helps them maintain their shape during baking.
Let the ganache cool and thicken completely before assembling the cookies.