Chocolate Filled Jack-O-Lantern Cookies

Chocolate Filled Jack-O-Lantern Cookies

Yield: 24 (1-inch) cookies
  • Prep Time: 10 minutes
  • Cook Time: 10 minutes
  • Cooling Time: 45 minues
  • Total Time: 1 hour, 5 minutes


For the Cookies:

  • 1 stick unsalted butter, softened
  • 2 tablespoons cream cheese, softened
  • ⅔ cup Swerve
  • 1 teaspoon vanilla
  • Orange food coloring, as needed (optional)
  • 1 ¾ cups almond flour
  • ¼ cup coconut flour
  • ¼ teaspoon cinnamon
  • ¼ teaspoon salt

For the Filling:


  1. Preheat the oven to 325°F. Line 2 cookie sheets with parchment paper.
  2. In a medium bowl, beat together the butter, cream cheese, Swerve, vanilla, and food coloring with an electric mixture until fully mixed.
  3. Add the almond flour, coconut flour, cinnamon, and salt.
  4. Beat, once more, until the mixture is completely mixed.
  5. Roll the dough between 2 pieces of parchment paper until about ¼-inch thick.
  6. Using a pumpkin cookie cutter, cut the dough into cookies.
  7. Carefully transfer the dough to the cookies sheets using a spatula.
  8. Bake the cookies on the middle-top rack of the oven until just slightly browned around the edges, about 7 minutes for 1-inch cookies. Adjust baking time, as needed.
  9. Allow the cookies to cool completely on the cookie sheet, about 30 minutes.
  10. The cookies will firm as they cool.
  11. When the cookies are cool, make the ganache.
  12. Place the chopped semi-sweet bar in a medium bowl with the heavy cream and microwave in 30-second intervals, stirring in between, until melted.
  13. Allow the ganache to cool until it has thickened, then transfer to a piping bag.
  14. Pipe a small amount of filling onto half of the cookies, then top with the other half.
  15. Chill the cookies until the ganache is firm, about 10 minutes.
  16. Enjoy right away or store in an airtight container in the refrigerator.