Activate the Yeast:Warm milk to 100–110°F. Stir in yeast and let sit 5–10 minutes until foamy.
Make the Dough:Add melted butter, sugar, eggs, and vanilla. Mix well. Add flour and salt, kneading for 8–10 minutes until smooth and elastic.
First Rise:Place dough in a greased bowl, cover, and let rise 60–90 minutes or until doubled in size.
Prepare Filling:Mix melted butter, brown sugar, cinnamon, cocoa powder, and crushed Oreos until combined.
Roll & Fill:Roll dough into a 12×18-inch rectangle. Spread filling evenly over the dough.
Slice & Roll: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!)
Second Rise:Cover and let rise for 30 minutes.
Bake:(Optional) Pour ¼ cup heavy cream over the rolls before baking for maximum softness. Bake at 350°F for 20–25 minutes until golden.
Make Frosting:Beat cream cheese, butter, and vanilla until smooth. Add powdered sugar, milk, and crushed Oreos. Mix just until incorporated.
Frost & Serve:Spread frosting on warm rolls. Garnish with extra Oreo crumbs if you’re feeling fancy.