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Chocolate Cinnamon Rolls

Chocolate cinnamon rolls are filled with cocoa, cinnamon, brown sugar, and semisweet chocolate chips, then baked until golden and topped with cream cheese frosting. The soft, fluffy rolls rise twice and are served warm.
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Prep Time 35 minutes
Cook Time 30 minutes
Proofing, rising, and cooling 2 hours 35 minutes
Total Time 3 hours 40 minutes
Servings: 12 servings
Course: Breakfast
Cuisine: American
Calories: 480
Ingredients Equipment Method Notes

Ingredients
  

For the dough and filling
  • 0.75 cup whole milk
  • 2.25 tsp active dry yeast
  • 0.25 cup granulated sugar
  • 1 egg large, room temperature
  • 1 egg yolk large, room temperature
  • 14 tbsp unsalted butter softened and divided: 4 tablespoons for the dough, 8 tablespoons for the filling, 2 tablespoons for the frosting
  • 3.5 cup all-purpose flour plus up to 0.25 cup for dusting
  • 1 tsp kosher salt
  • 1 tbsp neutral oil divided: 1 teaspoon for the bowl and 2 teaspoons for the baking dish
  • 0.75 cup light brown sugar packed
  • 2 tbsp unsweetened cocoa powder
  • 1 tbsp ground cinnamon
  • 1 cup semisweet chocolate chips
For the frosting
  • 4 oz cream cheese softened
  • 1 cup powdered sugar
  • 1 tsp vanilla extract
  • 1 tbsp whole milk

Equipment

  • 1 9x13-inch baking dish

Method
 

Make the dough
  1. Warm the milk to 105–110°F.
  2. Stir in the yeast and granulated sugar.
  3. Let stand for 5–10 minutes until foamy.
  4. Stir in the egg and egg yolk, then 4 tablespoons of the softened butter.
  5. Add 3 1/2 cups flour and the salt, and mix until a shaggy dough forms.
  6. Knead on a lightly floured surface for 8–10 minutes until smooth and elastic.
  7. Grease a large bowl with 1 teaspoon oil, add the dough, and turn it to coat.
  8. Cover and let rise in a warm place for 1–1 1/2 hours, until doubled in size.
Fill and shape the rolls
  1. Mix the brown sugar, cocoa powder, and cinnamon in a small bowl.
  2. Punch down the dough.
  3. Roll it on a lightly floured surface into a 12x18-inch rectangle, using up to the additional 1/4 cup flour as needed.
  4. Spread 8 tablespoons softened butter over the dough.
  5. Sprinkle the sugar mixture evenly over it.
  6. Scatter the chocolate chips on top.
  7. Grease a 9x13-inch baking dish with the remaining 2 teaspoons oil.
  8. Roll the dough up tightly from a long edge.
  9. Cut into 12 equal rolls.
  10. Arrange the rolls cut side up in the dish.
  11. Cover and let rise for 30–45 minutes, until puffy.
  12. Near the end of the rise, heat the oven to 350°F.
Bake the rolls
  1. Bake for 25–30 minutes, until golden brown and the centers are baked through.
  2. Let the rolls cool in the dish for 10 minutes.
Make the frosting
  1. Beat the cream cheese and the remaining 2 tablespoons softened butter until smooth.
  2. Beat in the powdered sugar, vanilla, and milk.
  3. Spread the frosting over the warm rolls and serve.

Notes

For soft rolls, knead until the dough is smooth and elastic and let it rise until doubled. Store covered in the refrigerator for up to 3 days; freeze unfrosted rolls for up to 2 months. For a dairy-free swap, use plant-based milk, butter, and cream cheese, plus dairy-free chocolate chips.