Start with the dough. In a large bowl, whisk together the flour, sugar, yeast, and salt. Make sure to break up any lumps in the flour.
Warm your milk until it feels like hot bath water (about 110°F). If it’s too hot, let it cool a bit – you don’t want to kill the yeast. Mix in the melted butter and eggs until well combined.
Pour the wet ingredients into the dry ingredients. Mix with a wooden spoon until a shaggy dough forms, then turn it onto a floured surface. Knead for about 8-10 minutes until the dough becomes smooth and springs back when you poke it with your finger.
Place the dough in a lightly oiled bowl, cover with plastic wrap, and let rise in a warm spot for about 1 hour, or until doubled in size.
While the dough rises, crush your Oreos for the filling. Don’t pulverize them into dust – you want some small chunks for texture. Mix them with the sugar and cinnamon in a bowl.
Once doubled, punch down the dough and roll it out on a floured surface into a 16×20-inch rectangle.
Spread the softened butter evenly over the dough, leaving a 1/2-inch border along one long edge. The butter should be very soft but not melted.
Sprinkle the Oreo-cinnamon mixture evenly over the butter. Press it gently into the butter so it sticks.
Starting from the long edge (without the border), roll the dough tightly into a log, pinching the seam to seal. If the roll feels loose, that’s okay – you can tighten it by gently stretching and rolling.
Cut into 12 even pieces using unflavored dental floss or a sharp knife. Place them in a greased 9×13-inch baking pan, leaving some space between each roll.
Cover and let rise again for about 30-45 minutes, until puffy and touching each other.
Preheat your oven to 350°F while they’re rising. Bake for 22-25 minutes, or until the tops are golden brown and a thermometer inserted into the center roll reads 190°F.
For the frosting, beat the softened cream cheese and butter until fluffy – about 2 minutes. Add the powdered sugar gradually (to avoid a sugar cloud), then beat in the vanilla. Fold in the crushed Oreos last.
Let the rolls cool for just 5-10 minutes before frosting. You want them warm enough so the frosting gets a little melty, but not so hot that it completely liquifies.