Mix dough: Mix all the dough ingredients together by hand or in a stand mixer with a dough hook. Knead dough on the counter or in the mixer for just a minute or two until the dough comes together forming a soft, pliable dough. If the dough is sticky, add a little extra flour.
Bulk Fermentation: Place the dough in a bowl and cover. Let the dough rise until doubled in size in a warm spot. At 78-80F this takes 8-9 hours.
Mix up the Filling: Near the end of bulk fermentation, mix up the filling. Crush the Oreo® cookies by hand or in a blender, then mix with brown sugar.
Shape: Grease a 9 by 13 inch pan. Punch down the dough and roll it into an approximate 18 by 12 inch rectangle. Spread the softened butter and then evenly sprinkle the Oreo® filling. Starting with the dough closest to you, roll up the chocolate roll and pinch together the seam. Flip over, seam side down. Cut the long log of dough into 12 pieces and nestle together in the pan. Cover the pan and set in a warm 80ºF place to rise.
Second Proof: Once the rolls are puffed up and risen, about 1-2 hours later, they are ready to bake. Do not proceed forward until the rolls have risen or the rolls will be dense.
Bake: Preheat the oven to 350ºF. Bake for about 25-30 minutes until baked all the way through and rolls register 190ºF.
Cookies & Cream Icing: While the rolls bake, crush 3 Oreo® cookies in a blender or by hand. In a medium bowl, beat butter and cream cheese until smooth. Mix in the vanilla, powdered sugar and crushed Oreo® cookies. Slowly add the milk until you reach your desired consistency. Spread on the warm rolls. Break up the remaining 6 cookies in larger chunks and sprinkle on top of the icing.
