Prepare the Dough: In a large bowl, whisk together flour, sugar, yeast, and salt. Add warm milk, melted butter, and egg, mixing until a soft dough forms. Knead for about 5 minutes until smooth. Place the dough in a greased bowl, cover, and let rise for 1 hour or until doubled in size.

Make the Filling: In a small bowl, mix brown sugar and cinnamon. Roll out the dough into a 12×16-inch rectangle. Spread softened butter over the dough, then sprinkle with the cinnamon sugar mixture. Evenly distribute the crushed Oreos on top.

Roll and Cut: Roll the dough tightly from the long side, then slice into 10-12 rolls. Place the rolls in a greased 9×13-inch baking dish. Cover and let rise for 30 minutes.

Bake: Preheat oven to 350°F (175°C). Bake the cinnamon rolls for 20-25 minutes until golden brown.

Make the Glaze: In a bowl, whisk together powdered sugar, milk, and vanilla extract until smooth. Drizzle over warm cinnamon rolls and top with crushed Oreo cookies.

Serve: Enjoy warm for the best flavor.