Prepare the Filling: In a medium bowl, mix together light brown sugar, black cocoa powder, and ground cinnamon until fully combined. Set aside.

Combine the Dry Ingredients: In a large bowl, whisk together all-purpose flour, instant dry yeast, and fine salt.

Prepare the Wet Ingredients: Warm whole milk, unsalted butter, and granulated sugar until the butter is melted.

Form the Dough: Add warm milk mixture to dry ingredients and mix until sticky dough forms. Adjust with more flour if needed.

Introduce the Oreo Flavor: Fold in crushed Oreos into the dough evenly.

Allow the Dough to Rest: Cover dough with plastic wrap and let it rest for 10 minutes at room temperature.

Roll Out the Dough: On a lightly floured surface, roll the dough into a 12x18 inch rectangle.

Add the Filling: Spread softened unsalted butter, then sprinkle the cinnamon filling and the remaining crushed Oreos.

Roll and Cut the Logs: Roll the dough tightly, sealing the filling and cutting into 9 equal pieces.

Let the Rolls Rise: Place cut rolls in a greased pan and let rise in a turned-off oven for about 30 minutes.

Bake to Perfection: Preheat oven to 350°F and bake the rolls for 26-30 minutes until golden brown.

Prepare the Glaze: Mix powdered sugar and vanilla extract until smooth; adjust consistency with milk if necessary.

Drizzle and Serve: Drizzle glaze over cooled rolls and let set before serving.