Pour milk, sugar and yeast into a large mixing bowl, stir together with a wooden spoon or dough whisk and let sit 10-15 minutes or until yeast is bubbly.
Add butter and eggs and mix together again.
Add salt and 2 cups of flour and mix. Continue adding flour in ½ cup increments until dough forms a ball and pulls away from sides of the bowl.
Pour dough out onto a floured surface and knead for 3- 5 minutes, incorporating more flour if needed. Dough should not be sticky, but more of a soft and tacky feel.
Place dough in greased bowl, cover with a cloth and let rise until doubled in size, anout 1½ hours.
Punch dough down and roll onto a floured surface. I try for a rectangle that is about 14x18.
Spread the room temperature butter into a thin and even layer, leaving about ½ inch on the bottom of the dough untouched so it can hold together.
Sprinkle with the brown sugar, being careful for to tear the dough while you spread it. Then with cinnamon, black cocoa powder and oreo cookie crumbs.
Working from the long 18 inch end of the dough, tightly roll it up into a log. Place your hands at each end of the side and give it a gentle squeeze to help compact the dough. It may have stretched out a bit during the rolling process so this brings it back together.
Cut the dough into 12 rolls total. I like to make little marking first to help make sure they are all about the same size.
Place the rolls in a greased 9×13 pan (you could also use two 9″ round pans, placing 6 rolls in each). It’s OK if all of the rolls are touching. *If wanting to bake the following day read notes down below for instructions.
Place in a warm spot, cover and let rise again until doubled in size. This takes about 45-60 minutes depending on how warm it is. You can always put them in your oven with the light on to help with warmth, but make sure you take them out to preheat your oven.
Preheat oven to 375 F.
Bake for 14-18 minutes or until the tops are a light golden brown. While they cool, make the frosting.