Heat the milk until it’s warm to the touch, about 100–110°F (37–43°C). Stir in the granulated sugar and sprinkle the active dry yeast over the surface. Let sit for 5–10 minutes until foamy and fragrant.

Whisk the melted butter and eggs into the foamy milk. Combine the flour and salt in a large bowl or mixer bowl. Add the wet mixture to the flour and mix until a soft, slightly tacky dough forms. Knead 6–8 minutes by hand or 4–5 minutes on medium speed until smooth and elastic.

Place dough in a lightly oiled bowl, cover with plastic or a damp towel, and let rise in a warm spot until doubled, about 60–90 minutes depending on room temperature.

Punch down the dough and roll it into a 12 x 18-inch rectangle. Brush with melted butter, sprinkle the cinnamon and dark brown sugar mixture evenly, then drizzle or dust with the Dutch-process cocoa for depth. Press 1 cup of chopped Oreos and 1 1/2 cups crushed Oreos into the filling layer, leaving a 1/2-inch border.

Tightly roll the dough from the long edge into a log. Cut into 12 equal pieces with a sharp knife or dental floss for clean slices. Place rolls in a buttered 9 x 13 pan, cover, and let rise 30–45 minutes until noticeably puffy.

Preheat oven to 350°F (175°C). Bake rolls for 20–25 minutes until golden brown and set in the centers.

Meanwhile, beat the cream cheese and heavy cream until smooth, add powdered sugar and vanilla, then fold in finely crushed Oreos. Spread the icing over warm rolls.