In a medium bowl, combine light brown sugar, black cocoa powder, and ground cinnamon. Stir well until evenly mixed, ensuring there are no lumps.

Using a stand mixer fitted with a dough hook, mix 3.5 cups of all-purpose flour, instant dry yeast, and fine salt at low speed. Meanwhile, warm the whole milk with granulated sugar and unsalted butter in a saucepan over low heat until melted and just warm. Gradually mix the warm milk mixture into the flour mixture until a sticky dough begins to form.

Add the large egg to the sticky dough and mix at medium speed until it's fully incorporated. If the dough remains too sticky, sprinkle in a little more flour, one tablespoon at a time, until the dough is tacky but no longer sticks to your fingers.

Fold the crushed Oreos gently into the dough using a spatula or wooden spoon, ensuring they're evenly distributed throughout. Cover the bowl with a kitchen towel and let the dough rest for about 10 minutes.

On a lightly floured surface, roll out the dough into a rectangle approximately 12x18 inches in size. Spread softened unsalted butter evenly over the rolled-out dough, then sprinkle your previously prepared filling and additional crushed Oreos on top.

Starting from one long edge, carefully roll the dough tightly into a log. Once rolled, slice it evenly into 9 pieces using a sharp knife or dental floss for clean cuts. Place the slices into a greased 9x13 inch baking pan.

To allow the rolls to rise, place the pan in a warm (turned-off) oven for 30 minutes.

Preheat your oven to 350°F (175°C). Once preheated, bake the rolls for 26-30 minutes or until they are golden brown across the tops.

In a medium bowl, whisk together melted butter, powdered sugar, whole milk, and artificial vanilla extract until you achieve a smooth consistency.

Allow the baked Oreo Cinnamon Rolls to cool slightly in the pan for about 5 minutes. Drizzle the prepared vanilla glaze generously over the top.