Step 1: Prepare the Tangzhong

Begin by preparing the tangzhong, a technique that helps keep the rolls moist and fluffy. In a small saucepan, combine 3/4 cup of water and 1/4 cup of all-purpose flour. Whisk them together until the mixture forms a smooth, paste-like consistency. Cook the mixture over medium heat, whisking constantly, for about 4-5 minutes. Once it thickens and reaches a paste-like consistency, remove the tangzhong from the heat and set it aside to cool.

Step 2: Make the Dough

In the bowl of a stand mixer, combine 3 1/2 cups of all-purpose flour, 1/3 cup of granulated sugar, 2 teaspoons of instant yeast, 1/4 cup of Oreo cookie crumbs, and 3/4 teaspoon of fine sea salt. Mix the dry ingredients until they’re well incorporated.

Next, add 1/2 cup of warm whole milk, 1 large egg (at room temperature), 1/2 teaspoon of vanilla extract, and the prepared tangzhong to the dry ingredients. Using the dough hook attachment, mix the ingredients on low speed for about 2 minutes until the dough forms a shaggy ball.

Now, add 4 tablespoons of softened unsalted butter, one tablespoon at a time. Allow each tablespoon of butter to fully incorporate into the dough before adding the next one. This helps achieve a smooth and buttery dough. Continue mixing the dough on low speed until it becomes smooth and elastic. If the dough feels too sticky or wet, add flour, one tablespoon at a time, until it comes together. If the dough is too dry, add a little milk, about half a tablespoon at a time.

Once the dough is smooth, remove it from the bowl and shape it into a round ball. Place it in a lightly buttered bowl, seam side down, and cover it with plastic wrap. Let the dough rise in a warm place for about 45-60 minutes, or until it has doubled in size.

Step 3: Roll Out the Dough

After the dough has risen, turn it out onto a lightly floured surface. Using a rolling pin, roll the dough into a 14×18 inch rectangle, with the long side facing you. The dough should be about 1/4 inch thick. Be sure to keep the surface lightly floured to prevent sticking.

Step 4: Make the Filling

In a small bowl, combine 2/3 cup of dark brown sugar (or light brown sugar), 4 tablespoons of softened unsalted butter, 1/3 cup of Oreo cookie crumbs, 1 tablespoon of black cocoa powder, and 1/4 teaspoon of ground cinnamon. Mix these ingredients together until they form a smooth paste. This will be the filling for your cinnamon rolls.

Step 5: Assemble the Cinnamon Rolls

Spread the Oreo filling evenly over the dough, leaving a 1/2 inch border at the top and bottom of the rectangle. Use an offset spatula to spread the filling smoothly over the dough, ensuring that each section is covered.

Once the filling is spread, it’s time to roll up the dough. Starting at the long edge of the rectangle, carefully roll the dough away from you into a tight cylinder. Be sure to pinch the seam at the end of the roll to prevent the filling from leaking out. After rolling the dough, use a pizza cutter or sharp knife to slice it into 12 equal pieces, each about 1 1/2 inches wide.

Step 6: Second Rise

Place the cinnamon rolls into a 9×13 inch baking pan lined with parchment paper. Be sure to arrange them so they’re snug against each other, which helps them rise evenly. Cover the pan with plastic wrap and let the rolls rise in a warm spot for 45-60 minutes, or until they’ve doubled in size.

Step 7: Bake the Cinnamon Rolls

Preheat the oven to 325°F (163°C). Once the cinnamon rolls have finished their second rise, remove the plastic wrap and place the pan in the preheated oven. Bake the rolls for 20-25 minutes, or until they’re golden brown on top. The aroma of cinnamon and cocoa will fill your kitchen, signaling that the rolls are ready to come out.

Step 8: Make the Frosting

While the cinnamon rolls are cooling, make the cream cheese frosting. In a medium bowl, combine 4 tablespoons of softened unsalted butter and 1 ounce of softened cream cheese. Using a hand mixer or stand mixer, beat the butter and cream cheese together until they’re smooth and creamy. Gradually add 1 cup of powdered sugar, mixing until combined. Finally, add 3 tablespoons of heavy cream and mix until the frosting is smooth and fluffy.

Step 9: Frost the Cinnamon Rolls

Once the cinnamon rolls have cooled slightly, spread the cream cheese frosting generously over the top of each roll. The frosting will melt into the warm rolls, adding a creamy, tangy layer of sweetness.

Step 10: Add the Finishing Touches

To finish off these Cookies and Cream Cinnamon Rolls, sprinkle some Oreo crumbs or chopped Oreos over the top of the frosting. This adds a crunchy texture and enhances the cookies and cream flavor of the rolls.