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Jack O'Lantern Cookies | Bake to the roots

Jack O’Lantern Cookies with Dulce de Leche

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  • Author: Bake to the roots
  • Prep Time: 45m
  • Cook Time: 12m
  • Total Time: 3h
  • Yield: 12
  • Category: Cookies
  • Cuisine: American


Delicious and not so scary Halloween cookies for a crowd with a sweet tooth: Jack O’Lantern Cookies with Dulce de Leche filling. So good!


For the dough:
3/4 cup (170g) butter, softened
1/2 cup (100g) brown sugar
1 tsp. vanilla extract
1 medium egg
2 1/4 cups (300g) all-purpose flour, plus more
1/2 tsp. baking soda
1/2 tsp. ground cinnamon
1/4 tsp. ground ginger
1/4 tsp. salt
pinch of ground nutmeg
For the decoration/filling:
2 tbsp. butter
3 tbsp. cinnamon sugar
3.5 oz. (100g) dulce de leche
0.7 oz. (20g) milk chocolate, melted


1. Add the butter, brown sugar, and vanilla extract to a large bowl and mix until light and fluffy. Add the egg and mix until well combined. Mix the flour with baking soda, ground cinnamon, ground ginger, salt, and nutmeg – add to the bowl and mix until just combined. If the dough seems too sticky add some more flour and mix in. The dough should be soft, but not sticky. Cover the bowl and place in the fridge for about 1 hour.
2. Roll out the dough on a well-floured surface and cut out pumpkin-shaped cookies – if you have a cookie cutter use that one, if not draw a pumpkin on a piece of paper, cut that out and use it as the shape to cut out the cookies. Make sure you have an even number of cookies. Place the cutout cookies on a floured board and place in the fridge for another 30 minutes or so.
3. Preheat the oven to 350°F (180°C). Line a baking sheet with baking parchment. Place the cooled cookies on the baking sheet with some space in between and bake for 9-12 minutes until lightly golden in color. Take out of the oven and let cool down on the baking sheet for some time, then transfer to a wire rack and let cool down completely.
4. Add the butter to a small pot and bring to a boil. Let cook until you can see dark spots on the bottom of the pot and the butter starts smelling a bit nutty – be careful, the butter tends to splash a lot. Take off the heat and let cool down for several minutes. Brush the nicer looking cookies (should be half of the amount of all cookies) with the melted butter and sprinkle with the cinnamon sugar. Set aside to dry a bit. To assemble the sandwich cookies spread about 1 teaspoon of dulce de leche on the bottom parts of the cookies (the ones you did not sprinkle with the cinnamon sugar) and press the sugary cookie on top to create a pumpkin sandwich cookie.
5. Melt the chocolate and fill into a small piping bag. Cut off the tip and pipe a typical Halloween pumpkin face on each cookie sandwich. Let dry. Store in an airtight container for up to 4 days.


Adapted from