01 -
Pour the warm milk into a large mixing bowl and stir in the sugar and yeast. Let this mixture sit for about 10-15 minutes until it gets nice and bubbly - this tells you your yeast is alive and ready to work its magic!
02 -
Add the softened butter and eggs to your yeast mixture and mix everything together. The butter might look a bit lumpy at this stage, but don't worry about that - it'll incorporate as you add the flour.
03 -
Now add the salt and 2 cups of flour to the bowl. Mix until combined, then continue adding the remaining flour in ½ cup increments until the dough forms a ball and starts pulling away from the sides of the bowl. You might not need all the flour, or you might need a touch more - trust your instincts and go by how the dough feels.
04 -
Turn your dough out onto a floured surface and get those hands working! Knead for about 3-5 minutes, adding small amounts of flour if the dough feels too sticky. You're looking for a dough that feels soft and a bit tacky but doesn't stick to your hands in a gluey mess.
05 -
Place your kneaded dough in a greased bowl, cover it with a clean kitchen towel, and let it rise in a warm spot until it doubles in size. This usually takes about 1½ hours, but could be quicker or slower depending on how warm your kitchen is.
06 -
Once the dough has doubled, give it a quick punch to deflate it, then roll it out on a floured surface into a rectangle about 14×18 inches. Try to keep the edges as even as possible for uniform rolls.
07 -
Spread the softened butter in a thin, even layer over the dough, leaving about ½ inch at the bottom edge bare (this helps seal the roll). Sprinkle the brown sugar evenly over the butter, then dust with cinnamon and black cocoa powder. Finally, scatter the crushed Oreo cookie crumbs all over. The black cocoa really gives these that true Oreo flavor!
08 -
Starting from the long (18-inch) edge, roll the dough into a tight log. When you reach the end, pinch the seam to seal it. Place your hands at each end of the log and give a gentle squeeze to compact the dough a bit - this helps keep your filling from spilling out when you cut.
09 -
Using a sharp knife or unflavored dental floss, cut the log into 12 equal rolls. I like to make small marks first to ensure they're all about the same size. Place the rolls in a greased 9×13 inch baking pan - it's fine if they're touching each other.
10 -
Cover the pan with a towel and place it in a warm spot to rise again until the rolls have doubled in size and are all puffy and touching each other. This usually takes 45-60 minutes. If your house is cool, you can turn your oven light on (but not the oven itself) and place the pan in there for a warm, draft-free spot.
11 -
Preheat your oven to 375°F. Bake the rolls for 14-18 minutes, or until the tops are lightly golden brown and the centers are cooked through. While they're baking, your house will fill with the most amazing cookie-meets-cinnamon-roll aroma!
12 -
While the rolls cool slightly, mix together the softened butter, vanilla, powdered sugar, and enough cream or milk to reach your desired consistency. You want the frosting to be spreadable but not runny. Beat until it's smooth and creamy.
13 -
When the rolls have cooled for about 10 minutes (still warm but not piping hot), spread or drizzle the vanilla frosting over the top. While the frosting is still soft, sprinkle additional crushed Oreo cookies over the top for that perfect finishing touch and extra Oreo flavor.