In a small saucepan, heat the whole milk to 110°F. Once warm, sprinkle the active dry yeast and 1/4 teaspoon of sugar into the milk, stirring gently. Let it sit undisturbed for about 10 minutes until frothy.

In a stand mixer bowl, combine 4 cups of all-purpose flour, 1 teaspoon of kosher salt, 1/2 cup of granulated sugar, and 1/3 cup of ground Oreos. Pour in the frothy yeast mixture, along with 8 tablespoons of melted butter and 2 large eggs. Mix on low speed until combined, then knead with the dough hook for about 5 minutes.

Transfer the dough into a lightly greased bowl, covering it with a clean kitchen towel. Place the bowl in a warm, draft-free spot and let it rise for approximately 1 hour, or until it has doubled in size.

Prepare the filling by mixing 1/2 cup of softened butter, 1/3 cup of dark brown sugar, 1 1/2 tablespoons of ground cinnamon, and 1 tablespoon of cocoa powder in a medium bowl. Blend until well combined and creamy.

Once the dough has risen, punch it down gently to release air. On a floured surface, roll the dough into a 14x18-inch rectangle. Spread the prepared filling evenly across the rolled-out dough. Sprinkle 1 cup of crushed Oreos on top.

Slice the dough into 12 strips, each about 1 1/2 inches wide. Roll each strip starting from one edge until you form a tight roll. Place them seam-side down in a greased 9x13-inch baking pan.

Cover the pan with a clean kitchen towel and let the rolls rise for another 30–40 minutes until they have doubled in size.

While the rolls are rising, preheat your oven to 375°F. Once fully risen, pour 1/2 cup of heavy cream evenly over the tops of the rolls. Bake for 20–22 minutes until they are beautifully golden brown.

In a mixing bowl, beat together 6 ounces of cream cheese, 1/2 cup of softened butter, 1 1/4 cups of powdered sugar, and 1 teaspoon of vanilla extract until smooth and creamy.

Once the cinnamon rolls are done baking, allow them to cool for about 10 minutes in the pan. Generously spread the creamy glaze over the warm rolls.