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Irresistible Oreo Stuffed Cinnamon Rolls

Fluffy, homemade sweet rolls stuffed with a dark cocoa filling and whole Oreo cookies, topped with a rich cream cheese icing.
Prep Time 30 minutes
Cook Time 25 minutes
Total Time 2 hours 40 minutes
Servings: 12 rolls
Course: Breakfast, Dessert
Cuisine: American, Baking
Calories: 480

Ingredients
  

Dough
  • 1 cup whole milk warmed to 110°F
  • 2.25 tsp active dry yeast 1 packet
  • 0.33 cup granulated sugar divided
  • 0.33 cup unsalted butter melted and slightly cooled
  • 1 large egg room temperature
  • 3.5 cups all-purpose flour plus more for dusting
  • 0.5 tsp salt
Oreo Filling
  • 0.5 cup unsalted butter softened
  • 0.5 cup brown sugar packed
  • 3 tbsp black cocoa powder or regular unsweetened cocoa
  • 1 package Oreo cookies standard size (some whole, some crushed)
Cream Cheese Icing
  • 6 oz cream cheese softened
  • 0.25 cup unsalted butter softened
  • 1.5 cups powdered sugar
  • 1 tsp vanilla extract
  • 1-2 tbsp milk to reach desired consistency

Equipment

  • Stand mixer or large bowl
  • 9x13 inch baking dish
  • Rolling Pin
  • Unflavored dental floss

Method
 

  1. In a bowl, combine warm milk, yeast, and 1 tbsp of sugar. Let sit for 5-10 minutes until frothy.
  2. Whisk in the remaining sugar, melted butter, and egg. Gradually add flour and salt, mixing until a dough forms.
  3. Knead the dough for 5-7 minutes until smooth and elastic. Place in a greased bowl, cover, and let rise for 1 to 1.5 hours until doubled in size.
  4. For the filling, mix softened butter, brown sugar, and cocoa powder until a paste forms. Crush about 10 Oreos into coarse crumbs.
  5. Punch down dough and roll into a 12x18 inch rectangle on a floured surface.
  6. Spread the cocoa butter paste evenly over the dough. Arrange 12-15 whole Oreos across the dough and sprinkle the crushed Oreos in between.
  7. Roll the dough tightly into a log starting from the long edge. Cut into 12 slices using unflavored dental floss.
  8. Place rolls in a greased 9x13 inch baking dish. Cover and let rise for 45-60 minutes until puffy.
  9. Bake at 350°F (175°C) for 22-28 minutes until golden brown.
  10. While baking, beat cream cheese and butter until smooth. Add powdered sugar, vanilla, and milk, beating until fluffy.
  11. Spread icing over warm rolls and top with additional crushed Oreos. Serve immediately.

Notes

To make ahead, prepare up to cutting the rolls and placing them in the pan. Cover and refrigerate overnight. Let sit at room temperature for 1.5-2 hours before baking.