In a medium bowl, mix together light brown sugar, black cocoa powder, and ground cinnamon until well combined. Set aside.

In a large mixing bowl, combine all-purpose flour, instant dry yeast, and fine salt. In a saucepan, heat whole milk, granulated sugar, and unsalted butter until just warm. Gradually add this mixture to the dry ingredients.

Transfer the dough to a floured surface and knead for about 5-7 minutes until elastic. Add flour one tablespoon at a time if too sticky.

Gently fold in the crushed Oreos into the kneaded dough and allow it to rest.

Cover the mixing bowl and let the dough rest for about 10-15 minutes.

Roll the rested dough into a large rectangle, spread butter, sprinkle the filling mixture, and any remaining crushed Oreos.

Roll the dough tightly from one long side and cut into 9 equal pieces with dental floss.

Cover the baking pan with foil and let the rolls rise in a warm oven for approximately 30 minutes.

Preheat your oven to 350°F while the rolls rise. Bake for 26-30 minutes until golden brown.

For the glaze, whisk together powdered sugar, melted butter, milk, and vanilla extract until smooth.

Let rolls cool for 5 minutes and drizzle the glaze generously over the warm rolls.