Oreo Stuffed Chocolate Chip Cookies

The only thing that could possibly be better than a good chocolate chip cookie is one that’s been stuffed with an Oreo cookie!  These Oreo Stuffed Chocolate Chip Cookies are decadent treats with the best kind of surprise inside.  

Helllloooo Friday.

We’ve made it through the workweek, through long commutes and tired routines with simply not enough coffee to wake our sleep deprived minds.  In my case, I’ve been grappling with shaking off the jetlag and regaining a shred of motivation after a great conference and mini vacation on the other side of the United States earlier this week, and getting back on track has been much more difficult than I thought.

You and I, we deserve a cookie.  A double cookie.  An Oreo Stuffed Chocolate Chip Cookie.

Make it two, please.

These cookies have been circulating the internet since the first time I ever logged on to Pinterest years ago (back when it was invite-only, anyone else remember that?).

I decided that they deserved a place on the blog with a from-scratch chocolate chip cookie recipe (no pre-made, store-bought dough here!), and so I got to work on a soft and chewy chocolate chip cookie recipe that could securely hold an Oreo Cookie.  I actually ultimately modified another stuffed cookie recipe that I had on the blog (this is not my first time stuffing one dessert inside another, not even close).

After only a few modifications, here we are.

While these cookies are pretty simple (make chocolate chip cookie dough, chill it briefly so that it’s manageable, roll it around an Oreo cookie, chill briefly again, bake, done), I do have some quick and easy tips before you get started:

• Chill the dough after making it, otherwise it will likely be too sticky to manage.  15 minutes should be sufficient, but if it’s still too sticky just return it to the fridge for another 10 minutes.  Don’t chill it too long, or it will be too firm to mold around your Oreos.
• Chill the dough again after you make your cookie balls.  This will keep them from spreading too much in the oven.  Only 15-30 minutes is needed in the freezer, but you can chill these longer.  If you intend to save them to bake later (longer than 30 minutes), just be sure to wrap them in plastic wrap and store in a Ziploc bag or airtight container.
• Know which way your Oreo cookie is facing. I can’t tell you how many times I’ve baked one of these only to end up with a big vertical lump thanks to an Oreo Cookie standing on its end right in the center.  As you mold the dough around each cookie, just be mindful of the direction your Oreo is facing, making a small indent or “x” on the top of each ball of dough could be a helpful reminder once you’ve rolled them.
• For pretty cookies, gently press additional chocolate chips onto the surface of each cookie after they come out of the oven.  This makes them look nice and keeps the cookie dough from requiring too may chips, which can make it difficult to roll the dough around your Oreos.

I also made a short (non-YouTube) video that you can see below to show you exactly how I make these Oreo stuffed cookies.

Are these videos helpful to you?  Do you prefer the short ones (like I have here) or the slightly longer YouTube ones (and can you guess which one I prefer filming!?  It’s the ones where you don’t see my face — I am so uncomfortable being on camera!).

Either way, enjoy!

Full printable recipe below the video

Oreo Stuffed Chocolate Chip Cookies

The only thing that could possibly be better than a good chocolate chip cookie is one that's been stuffed with an Oreo cookie!  These Oreo Stuffed Chocolate Chip Cookies are decadent treats with the best kind of surprise inside.  

5 from 14 votes

Print Pin Rate

Course: Dessert, cookies

Cuisine: American

Prep Time: 30 minutes

Cook Time: 13 minutes

Total Time: 43 minutes

Servings: 15 large cookies

Calories: 417kcal

Author: Sam Merritt

Ingredients

• 1 cup unsalted butter softened to room temperature (226g)1 cup unsalted butter softened to room temperature (226g)
• 1/2 cup sugar (100g)1/2 cup sugar (100g)
• 1 cup brown sugar tightly packed (200g)1 cup brown sugar tightly packed (200g)
• 2 large eggs room temperature2 large eggs room temperature
• 1 teaspoon vanilla extract (5ml)1 teaspoon vanilla extract (5ml)
• 3 cups all-purpose flour (380g)3 cups all-purpose flour (380g)
• 2 teaspoons cornstarch2 teaspoons cornstarch
• 1 teaspoon baking soda1 teaspoon baking soda
• 1 teaspoon baking powder1 teaspoon baking powder
• 1/2 teaspoon salt1/2 teaspoon salt
• 1 1/2 cup semisweet chocolate chips divided (255g)1 1/2 cup semisweet chocolate chips divided (255g)
• 20 Oreo Cookies divided20 Oreo Cookies divided

Instructions

• In the bowl of a stand mixer (or in large bowl using electrical mixer), cream together butter and sugars until light and fluffy. Scrape sides of bowl.
• Add eggs and vanilla extract. Beat until well-combined.
• In a separate bowl, whisk together flour, cornstarch, baking soda, baking powder, and salt.  
• Gradually add dry ingredients to wet, stirring until well-combined.
• Fold in 1 cup of chocolate chips, reserve remaining 1/2 for later.  
• Place 5 Oreo cookies in a small plastic bag and use a rolling pin or mallet to break into small pieces.  Use a spatula to fold cookie bits into dough.
• Cover dough and chill in refrigerator for 15-30 minutes.
• Scoop 1 ½ Tbsp of dough, flatten between your palms, and place on top of one Oreo cookie.  Wrap another 1 ½ Tbsp of dough around the bottom of the cookie and mold the dough around the cookie until it's completely covered (add more dough, if needed).  Repeat with remaining Oreo cookies.
• Place dough on a wax paper lined plate and freeze for 20-30 minutes.  Meanwhile, preheat oven to 375F (190C).
• Once dough has chilled and oven is preheated, place dough on parchment paper lined cookie sheet, spacing each cookie at least 2" apart, and bake on 375 for 11 minutes,
• Within 2 minutes of removing cookies from oven, gently nestle remaining chocolate chips on top of each cookie.  
• Allow to cool before enjoying.

Nutrition

Serving: 1cookie | Calories: 417kcal | Carbohydrates: 47g | Protein: 6g | Fat: 23g | Saturated Fat: 13g | Cholesterol: 62mg | Sodium: 239mg | Potassium: 204mg | Fiber: 3g | Sugar: 20g | Vitamin A: 428IU | Calcium: 38mg | Iron: 4mg

Tried this recipe?Mention @SugarSpun_Sam or tag #sugarspunrun!