Dark Chocolate Cookies with Dark Chocolate Fudge Filling: the perfect Christmas cookie to add to your holiday baking menu! 

While these cookies require an extra step or two above most Christmas cookie recipes, they are super simple. A layer of addicting dark chocolate fudge filling is sandwiched between two crispy chocolate cookies. Each amazing bite is better than the last one!

Let’s hop on this holiday baking bandwagon shall we? I mean there are only 22 days left until the big day. It’s time to get in those kitchens, crank up those ovens, and start baking up a storm. I have already spent my fair share of days in the kitchen whipping up some magical Christmas cookies, and I’m so not sad about it. Instead of getting super frustrated in the kitchen like I tend to do when I’ve been baking all day, I’ve tried to stay calm throughout the whole process. A marathon of Gilmore Girls playing on the TV in the background and keeping the fire ablaze (it’s been pretty effing cold here) have kept me sane. Lucky for you, cookies I can handle. Cupcakes and bread? Not so much.

These dark chocolate cookies with dark chocolate fudge filling are a new cookie recipe that I’ve decided to add to this year’s holiday baking menu. I tend to stick to what I know. Sometimes I’ll put different spins on my usual cookies, but this year I decided to get creative.

These cutout cookies are your typical cutout cookies. This has not changed. They are pretty traditional, but the filling is by far my favorite part. Maybe I can thank a 10-year-old Justine who most of the time licked the frosting off of each cupcake and put it back for this, but I tend to lean towards frosted things. What’s a good cookie without a good filling? It doesn’t exist my friends. It doesn’t exist.

Except for an hour of chilling time, these dark chocolate cookies are pretty self-explanatory. I tend to ALWAYS chill my cookie dough, even if I’m following a recipe that doesn’t require it. It definitely makes the dough easier to handle, so don’t skip this step! I hope you guys love this recipe as much as I do. Pair these cookies with a chocolate stout and enjoy the rest of your day! xo

Dark Chocolate Cookies with Dark Chocolate Fudge Filling

This recipe requires at least 1 hour of chilling, inactive time!

Print Pin Rate

Prep Time: 1 hour 20 minutes

Cook Time: 8 minutes

Total Time: 1 hour 28 minutes

Servings: 16 cookies

Ingredients

For the Dark Chocolate Cookies

• ▢ 1 cup unsalted butter softened to room temperature
• ▢ 3/4 cup granulated sugar
• ▢ 1/2 cup light brown sugar
• ▢ 1 1/2 cup unsweetened cocoa powder
• ▢ 5 ounces dark chocolate chips melted and cooled slightly
• ▢ 1/2 teaspoon baking powder
• ▢ 1/2 teaspoon kosher salt
• ▢ 2 large room temperature eggs
• ▢ 2 tablespoons milk
• ▢ 1 teaspoon vanilla extract
• ▢ 1 1/2 cup all-purpose flour

For the Dark Chocolate Fudge Filling

• ▢ 3/4 cup dark chocolate chips melted and cooled slightly
• ▢ 4 ounces cream cheese softened to room temperature
• ▢ 1/2 cup confectioner's sugar
• ▢ 1/2 teaspoon vanilla extract
• ▢ 1 tablespoon milk

Instructions

• ▢
  In the bowl of your stand mixer (with paddle attachment fixed) add the butter, granulated sugar and brown sugar. Mix until pale and creamy. Add the cocoa powder, melted chocolate, baking powder and salt. Mix until thoroughly combined. Beat in each egg, one at a time, and then mix in the milk and vanilla extract. Add the flour and mix until just combined. Do not over mix.
• ▢
  Divide the dough in two and wrap each separately in plastic wrap. Place in the fridge to chill for at least 1 hour.
• ▢
  Preheat your oven to 375 degree F and line two large cookie sheets with parchment paper or a silicone baking mat. Flour a work surface, and unwrap your cookie dough. Roll each portion out to 1/4 of an inch thick, then cut shapes out of the dough. I used a 2-inch star-shaped cookie cutter. Take half of your cut out cookies, and taking a small round cookie cutter cut out the center.
• ▢
  Place the cookies with the holes and without onto the prepared baking sheets. Bake the cookies for 7-8 minutes or until just firm on the edges. Remove from heat and transfer to a wire rack to cool completely.
• ▢
  While the cookies are cooling, prepare your dark chocolate fudge filling. In the bowl of your stand mixer (with paddle attachment fixed), combine the melted chocolate, cream cheese, confectioner's sugar, vanilla extract and milk. Mix until combined and the filling has reached a spreadable consistency.
• ▢
  Spread the filling onto the cookies without the cut out. Top with the cookies that have the cutouts. Store the cookies in an airtight container for about a week, and enjoy!