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Easy Jack-O-Lantern Pumpkin Pie Thumbprint Cookies

pumpkin pie thumbprint cookies - featured image

These Easy Jack-O’-Lantern Pumpkin Pie Thumbprint Cookies combine a buttery shortbread base with a creamy pumpkin pie filling, topped with adorable chocolate chip jack-o’-lantern faces. Perfect for Halloween parties, lunchboxes, or any fall gathering.

Ingredients

Scale
  • 1 cup (2 sticks) unsalted butter, softened
  • 2/3 cup granulated sugar
  • 1 large egg yolk
  • 1 teaspoon vanilla extract
  • 1 1/2 cups all-purpose flour
  • 1/2 teaspoon salt
  • 1/2 teaspoon baking powder
  • 1/2 cup pumpkin puree
  • 1/4 cup brown sugar, packed
  • 1 large egg yolk
  • 1 teaspoon pumpkin pie spice
  • 1/2 teaspoon vanilla extract
  • About 30 mini chocolate chips

Instructions

  1. Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper or silicone mats.
  2. In a large bowl, beat the softened butter and granulated sugar together until light and fluffy, about 2-3 minutes on medium speed. Scrape down the sides halfway through.
  3. Beat in the egg yolk and vanilla extract until just combined.
  4. In a separate small bowl, whisk together the flour, salt, and baking powder. Gradually add to the butter mixture, mixing on low speed until a soft dough forms. If too dry, add a teaspoon of cold water; if too sticky, add a tablespoon more flour.
  5. If the dough is too soft, chill in the fridge for 15-20 minutes.
  6. Scoop rounded tablespoons of dough and roll into balls. Place on prepared baking sheets about 2 inches apart. You should get about 20-24 cookies.
  7. Use your thumb or the back of a rounded teaspoon to make an indentation in the center of each dough ball, about 1/2 inch deep. Smooth any cracks gently with your fingers.
  8. In a small bowl, whisk together the pumpkin puree, brown sugar, egg yolk, pumpkin pie spice, and vanilla extract until smooth. The mixture should be thick but spreadable.
  9. Transfer the pumpkin filling to a small piping bag or a zip-top bag with the corner snipped off. Pipe the filling into each indentation, filling almost to the top but not overflowing.
  10. Bake for 12-14 minutes, or until the edges are lightly golden and the filling is set. Rotate the pans halfway through baking.
  11. As soon as the cookies come out of the oven, press two mini chocolate chips into the filling for eyes and a few more in a curved line for the mouth. Work quickly while the cookies are warm.
  12. Let the cookies cool on the baking sheets for 5 minutes, then transfer to a wire rack to cool completely.

Notes

Add chocolate chip faces while cookies are warm so they stick. If filling looks runny, add extra brown sugar to thicken. For best results, use room temperature butter and egg yolk. Cookies taste even better the next day.

Nutrition

Keywords: pumpkin pie thumbprint cookies, jack-o-lantern cookies, Halloween cookies, pumpkin cookies, thumbprint cookies, fall baking, easy Halloween treats