Warm milk to 100–110°F. Stir in yeast and let sit 5–10 minutes until foamy.
Add melted butter, sugar, eggs, and vanilla. Mix well. Add flour and salt, kneading for 8–10 minutes until smooth and elastic.
Place dough in a greased bowl, cover, and let rise 60–90 minutes or until doubled in size.
Mix melted butter, brown sugar, cinnamon, cocoa powder, and crushed Oreos until combined.
Roll dough into a 12×18-inch rectangle. Spread filling evenly over the dough.
Cut into 12 equal strips, roll each individually, and place in a greased 9×13 pan. (Save a little filling to spread on the bottom for extra gooeyness!)
Cover and let rise for 30 minutes.
(Optional) Pour ¼ cup heavy cream over the rolls before baking for maximum softness. Bake at 350°F for 20–25 minutes until golden.
Beat cream cheese, butter, and vanilla until smooth. Add powdered sugar, milk, and crushed Oreos. Mix just until incorporated.
Spread frosting on warm rolls. Garnish with extra Oreo crumbs if you’re feeling fancy.
