Chocolate Sandwich Cookies with Oreo Coffee Filling

OK friends, I think I’ve discovered my new favorite thing to make (and eat): COOKIE SANDWICHES! More specifically, these Chocolate Sandwich Cookies with Oreo Coffee Filling.

This sandwich cookie is based off of this cake recipe, and you better believe me when I say these are the best things ever.

It took a few tries to get this recipe right as flavor and eat-ability are key, but I finally landed on the perfect cookie and filling recipes that when combined, create the most delicious sandwich that is also easy to eat.

Plus, it’s hard to go wrong when you’re mixing chocolate, Oreos and coffee!

I hope you enjoy these Chocolate Sandwich Cookies with an Oreo Coffee Filling! Let me know in the comments below how they turned out or share a photo on Instagram and tag @homecourtbakes! 

XO,
Coco

Prep time: 4 hours (includes chill time)
Cook time: 12 minutes (per batch)
Total time: 5 hours and 30 minutes
Yields: ~20 cookies

Ingredients for the Chocolate Cookie:

• 113 grams (1/2 cup) unsalted butter at room temperature  
• 100 (1/2 cup) grams granulated sugar 
• 100 grams (1/2 cup) packed light brown sugar 
• 1 egg
• 4 grams (1 tsp) vanilla extract 
• 125 grams (1 cup scooped and leveled) all-purpose flour 
• 51 grams (1/2 cup plus 2 Tbsps) natural unsweetened cocoa powder
• 5 grams (1 tsp) instant espresso powder
• 4 grams (1 tsp) baking soda
• 3 grams (1/2 tsp) kosher salt 
• 1 Tbsp milk

Ingredients for the Oreo Coffee Filling:

This recipe will leave you with extra filling. If you don’t want extra, you can cut the recipe in half.

• 1 cup heavy cream
• 8 ounces full-fat cream cheese
• 3/4 cup confectioners’ sugar
• 1 tsp vanilla extract
• 12 Oreos, chopped (Double Stuf or regular)
• 1-3 Tbsps. instant espresso powder

Instructions:

Make the Chocolate Cookie:

• Using a hand or stand mixer fitted with a paddle attachment, cream the butter and sugars together on high until smooth, about 2-3 minutes. Scrape down the sides of the bowl.
• In a small bowl, combine the egg and vanilla extract. Add to the butter mixture and mix on high for 4-6 more minutes. Scrape down the sides of the bowl halfway through and again at the end. The dough should be homogenous and you shouldn’t see any pockets of unmixed butter or sugar. 
• In a separate bowl, mix the flour, cocoa powder, espresso powder, baking soda and salt. Add to the wet ingredients all at once and mix on low for about 30-45 seconds. Add the milk and then mix on low just until combined. The dough will be sticky.
• Using a cookie scooper or spoon, scoop the dough into balls and place on a baking sheet lined with parchment paper (or a plate). Cover the dough with plastic wrap or aluminum foil and chill in the refrigerator for at least 3 hours (or overnight).
• Preheat the oven to 350°F.
• Place the pieces of dough on a baking sheet lined with parchment paper a few inches apart. Bake for 12 minutes (or until the sides start to firm up and center is still soft). Depending on how your oven cooks, you may want to rotate the cookie sheet 180° halfway through to ensure your cookies are evenly cooked.
• Cool the cookies on the cookie sheet for 5 minutes before transferring to a wire rack to cool completely. 

Make the Oreo Coffee Filling:

• While the cookies are cooling, make the filling (note: you will need to mix ingredients in two separate bowls to start).
• In a medium bow, whip the cold heavy cream into stiff peaks on medium-high speed (about 4-5 minutes) using a hand or stand mixer fitted with a whisk attachment. Set aside.
• Using a hand or stand mixer fitted with the paddle attachment, beat the cream cheese on medium speed until smooth and creamy. Scrape down the sides and bottom of the bowl with a rubber spatula as needed. Add the confectioners’ sugar and vanilla extract and beat on medium-high speed until combined.
• Using your mixer on low speed or a rubber spatula, fold the whipped cream and chopped Oreos into the cream cheese mixture until combined. If using a spatula, this will take several turns to mix together. Combine slowly so you don’t deflate all the air in the whipped cream.
• Once the cookies are cooled, separate the cookies into pairs with each bottom cookie turned upside down. Using a cookie scooper or spoon, scoop the filling onto the center of each bottom cookie and then press the top cookie onto the filling. Chill the cookie sandwiches in the refrigerator for 30-60 minutes to allow the filling to firm up a bit.
• Enjoy!
  • Storage: These cookies are best stored in the refrigerator to keep the filling cool and firm.