Jack O Lantern Cookies Recipe

Ash Tyrrell

Jack O Lantern Cookies Recipe

I bake these Jack O Lantern cookies every single October, and by now my kitchen counter looks like a pumpkin patch exploded on it. I'm honestly not much of a candy person, but a soft chocolate cookie sandwiched with orange cream cheese frosting? That gets me every time. I first tried this idea on a whim a few Halloweens ago, and now it's become the one dessert my whole family asks for by name.

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Total Time 2 19

Servings: 15

Ingredients Method Notes

Ingredients

2 ½ cups all-purpose flour — gives the cookies enough structure to hold their pumpkin shape while baking
½ cup Dutch-process cocoa powder — richer and less acidic than natural cocoa so it pairs better with the tangy frosting
1 teaspoon baking powder — helps the cookies stay soft instead of turning out flat and hard
¼ teaspoon fine sea salt — balances the sweetness and makes the chocolate flavor pop
1 ½ sticks unsalted butter at cool room temperature — creaming this properly is key to a smooth, workable dough
1 cup granulated sugar — don't be tempted to cut this down it affects the texture as much as the sweetness
2 large eggs at cool room temperature — binds the dough and adds a bit of richness
1 teaspoon pure vanilla extract — rounds out the chocolate flavor nicely
4 ounces cream cheese at room temperature — softened cream cheese blends smoother and avoids lumpy frosting
4 tablespoons unsalted butter at room temperature — adds richness and helps the frosting hold its shape
2 teaspoons vanilla extract — a simple flavor boost that keeps the frosting from tasting flat
1 ½ cups powdered sugar sifted — sifting here is not optional, it keeps the frosting silky instead of gritty
A few drops orange gel food coloring — gel coloring gives a vibrant pumpkin shade without thinning out the frosting

Method

Sift the flour, cocoa powder, baking powder, and salt together in a bowl. In a separate large bowl, beat the butter and sugar until smooth, then mix in the eggs one at a time along with the vanilla. Slowly add the dry ingredients until a soft, cohesive dough forms.
Place the dough between two sheets of parchment paper and roll it out to about a quarter-inch thickness. Chill the rolled dough in the fridge for at least an hour, or in the freezer for about 30 minutes, until it feels firm to the touch.
Once firm, use your pumpkin cookie cutter to cut shapes from the dough and place them on your lined baking sheets. On half of the pumpkins, use your paring knife to carve out small triangle eyes and a mouth for that classic jack-o'-lantern face.
Pop your baking sheets of cut-out dough back in the fridge for another 30 minutes, or the freezer for 15 minutes. This step keeps the shapes from spreading and losing their crisp pumpkin outline once they hit the oven.
Bake at 350°F for 8 to 9 minutes, just until the cookies are set but not overdone. Let them cool on the baking sheet for a few minutes before transferring them to a wire rack to cool completely.
Beat the cream cheese, butter, and vanilla together until smooth, then gradually mix in the powdered sugar. Add a few drops of orange gel coloring until you reach your desired shade. Spread frosting onto the plain pumpkin cookies, then top each with a jack-o'-lantern face cookie to make your sandwich.

Notes

I always measure my flour with a kitchen scale, since even a little too much makes the dough dry and crumbly.
I let my butter sit out until it's truly at cool room temperature, not soft and greasy, or the dough turns out too sticky to roll.
I never skip chilling the dough twice, since it's the only thing that keeps my pumpkin shapes from losing their outline in the oven.
I use gel food coloring instead of liquid for the frosting, because liquid dye waters everything down and never gives me that bold pumpkin orange.
I like sifting my powdered sugar even when I'm in a rush, since it saves me from grainy frosting every time.