Ingredients
For the chocolate sugar cookies:
- 2 1/2 cups (318 grams) all-purpose flour
- 1/2 cup (50 grams) Dutch-process cocoa powder*
- 1 teaspoon baking powder
- 1/4 teaspoon fine sea salt
- 1 1/2 sticks (170 grams) unsalted butter, at cool room temperature
- 1 cup (200 grams) granulated sugar
- 2 large eggs, at cool room temperature
- 1 teaspoon pure vanilla extract
For the cream cheese frosting:
- 4 ounces (113 grams) cream cheese, at room temperature
- 4 tablespoons (57 grams) unsalted butter, at room temperature
- 2 teaspoons vanilla extract
- 1 1/2 cups (188 grams) powdered sugar, sifted (don't skip sifting!)
- Orange gel food coloring
Directions
Make the cookies:
-
In a medium bowl, sift together the flour, cocoa powder, baking powder, and salt.
-
In a large bowl, use an electric mixer to beat the butter and sugar on medium-high speed until smooth and well combined, 1 to 2 minutes. Add the eggs, one at a time, until well combined. Add the vanilla extract. On low speed gradually add the flour mixture and beat until thoroughly combined.
-
Place the dough in between two large pieces of parchment paper or silicone mats on a work surface. Roll the dough out to a 1/4-inch thickness. Chill in the refrigerator until firm, at least 1 hour, or in the freezer until firm, about 30 minutes.
-
Line large baking sheets with parchment paper. Use a 3 or 4-inch pumpkin cookie cutter to cut out shapes from the dough and place on prepared baking sheets. Use a small paring knife to carefully cut out the triangle eyes and mouth shapes in half of the pumpkins.**
-
Gently reroll remaining scraps of dough to a 1/4-inch thickness, cut out eyes and mouths in half of the pumpkins, and place on prepared baking sheets. If the sheet of dough softens too much at any point, place it back in the freezer or fridge until firm again before cutting and moving more shapes.
-
Chill the baking sheets of cut cookie dough in the refrigerator for 30 minutes or freezer for 15 minutes, or until dough is firm. Meanwhile, preheat the oven to 350°F.
-
Bake for 8 to 9 minutes, or until the cookies are set but not overbaked. Let cool on baking sheets for 5 minutes before removing to a wire rack to cool completely. Plain cookies can be stored in an airtight container at room temperature for up to 3 days or in the freezer for up to 2 months.
Make the cream cheese frosting:
-
In the bowl of a stand mixer fitted with the paddle attachment, beat the cream cheese, butter, and vanilla on medium-high speed until very light, creamy, and smooth, about 2 to 3 minutes. On low speed, gradually add in the sugar and beat until fluffy, about 2 minutes more. Add in a few drops of orange gel food coloring until desired shade is reached.
Assemble the sandwiches:
-
Place a dollop of cream cheese frosting on the center of the top of the plain pumpkin shaped cookies. Don’t frost the bottom side, otherwise the pumpkin stem shapes won’t line up. Place a jack o’lantern cookie on top of each, pressing down slightly to sandwich the filling. Serve or store in an airtight container at room temperature for up to 2 days (the sugar in the cream cheese frosting acts as a preservative, but they should not be stored at room temperature for longer than that).
Tessa’s cookie recipes are always a hit! My office loved them!!
Very cute and festive, tasted great!
Although a bit more time consuming than simple drop cookies, these Jack-O-Lantern cookies were fun and tasty!
Perfect Halloween cookie!Delish
So fun to make and super festive!
I have a bucket of Halloween cookie cutters so I decided to make this recipe. The dough came together quickly and was pretty easy to work with. The cookies held their shape well, I could identify the shape of each cookie unlike other cutout recipes out there. I feel like there’s something missing in terms of flavor but the frosting makes up for it.
Amazing cookies
Simply delicious. Great techniques for cutout cookies here. I’ve never been great at them but this recipe is fantastic!
My mom loved these! The slight sweetness of the cookie compliments the cream cheese icing perfectly.
I love so many of Tessa’s recipes but this one…not so much. Without a cookie cutter, cutting out the shapes was a pain and the 4” cookies were too big. Especially when you put two together. They probably would have been better with just one small cookie topped with her sugar cookie icing.
Super cute & delicious!
Delicious!! My dad said he could eat just the cookie by itself!
Just made this recipe and it’s great! It’s honestly one of the best cookies I’ve ever made.
This recipe was easy to follow and was a fun alternative to classic sugar cookies. I love the cream cheese filling and how it complements the chocolate cookies. They were delicious!
Very tasty and so cute!
Fun & tasty Halloween cookies! Rich chocolate cookie with cream cheese filling or frosting is a delicious combination.
Yummy and cute
Love this chocolate cookie recipe! Really easy and can be made into any shape. I will definitely make my next sandwich cookie smaller since each sandwich is already 2 cookies. It’s easiest to use with a paring knife while the dough is very cold for any cutouts.
For me, these weren’t the easiest to make as I am not that artistic, and my jack o lanterns came out a bit crooked, but they were delicious! Definitely would make them again as a cut out cookie, just not as a filled jack o lantern!
Loved making these! Simple, easy, fun … and very tasty!!
These came out so good!! A big hit with my family!