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Delicious chocolate cookie cinnamon rolls drizzled with icing and topped with chocolate chips.

Chocolate Cookie Cinnamon Rolls

These Chocolate Cookie Cinnamon Rolls combine the comforting warmth of cinnamon rolls with a rich chocolate cookie filling and a sweet glaze, creating an irresistible treat for any occasion.
Prep Time 45 minutes
Cook Time 25 minutes
Total Time 2 hours
Servings: 10 rolls
Course: Breakfast, Dessert
Cuisine: American
Calories: 450

Ingredients
  

For the Dough
  • 3.5 cups All-purpose flour plus more for dusting
  • 1/4 cup Granulated sugar
  • 2.25 teaspoons Active dry yeast
  • 1 cup Warm milk (105-115°F)
  • 1/4 cup Unsalted butter, melted
  • 1 teaspoon Salt
  • 1 Large egg
For the Filling
  • 1/2 cup Unsalted butter, softened
  • 1/2 cup Light brown sugar, packed
  • 1/4 cup Cocoa powder
  • 1 tablespoon Ground cinnamon
  • 1 cup Chocolate cookie crumbs from crushed chocolate cookies
For the Glaze
  • 1.5 cups Powdered sugar
  • 2-3 tablespoons Milk
  • 1/2 teaspoon Vanilla extract

Equipment

  • Large mixing bowl
  • Rolling pin
  • 9x13 inch baking dish
  • Small bowl
  • Whisk

Method
 

Prepare the Dough
  1. In a large bowl, dissolve yeast and a pinch of sugar in warm milk, then let it sit for 5-10 minutes until foamy. Whisk in the remaining granulated sugar, melted butter, salt, and egg.
  2. Gradually add the flour, mixing until a shaggy dough forms, then turn it out onto a lightly floured surface. Knead for 5-7 minutes until the dough is smooth and elastic.
First Rise
  1. Place the dough in a lightly oiled bowl, cover with plastic wrap, and let it rise in a warm place for 60-90 minutes, or until doubled in size.
Assemble the Rolls
  1. Punch down the risen dough and roll it into a 12x18-inch rectangle on a lightly floured surface. In a small bowl, mix softened butter, brown sugar, cocoa powder, cinnamon, and chocolate cookie crumbs to create the filling.
  2. Spread the filling evenly over the dough, leaving a small border on one long edge. Tightly roll up the dough from the opposite long edge and pinch the seam to seal it.
  3. Slice the log into 10-12 equal pieces and arrange them in a greased 9x13-inch baking dish.
Second Rise & Bake
  1. Cover the baking dish and let the rolls rise again in a warm place for 30-45 minutes, or until puffy. Preheat your oven to 375°F (190°C) during this time.
  2. Bake for 20-25 minutes, or until golden brown and cooked through. If rolls are browning too quickly, you can loosely tent them with foil.
Prepare and Glaze
  1. While the rolls are cooling slightly, whisk together powdered sugar, milk, and vanilla extract until smooth to make the glaze. Add more milk if a thinner consistency is desired.
  2. Drizzle the glaze generously over the warm cinnamon rolls before serving. Enjoy warm.

Notes

For extra richness, use whole milk in the dough. You can also add a pinch of espresso powder to the filling for a deeper chocolate flavor.