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Triple Chocolate Cinnamon Rolls with Chocolate Cream Cheese Frosting

Close-up of gooey chocolate cinnamon rolls generously covered in chocolate frosting and mini chocolate chips.

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Make soft, gooey chocolate cinnamon rolls from scratch using a rich chocolate dough, a decadent chocolate-cinnamon filling, and top them with a thick chocolate cream cheese frosting. This recipe delivers bakery-style rolls perfect for brunch or dessert.

Ingredients

Scale
  • 1 cup whole milk, warmed to 110°F
  • 2 1/4 teaspoons active dry yeast
  • 1/2 cup granulated sugar, divided
  • 1/4 cup unsalted butter, melted
  • 1 large egg
  • 3 1/2 cups all-purpose flour, plus more for dusting
  • 1/2 cup unsweetened cocoa powder
  • 1 teaspoon salt
  • 1 teaspoon ground cinnamon
  • 1/2 cup unsalted butter, softened (for filling)
  • 1 cup packed light brown sugar (for filling)
  • 1/2 cup semi-sweet chocolate chips (for filling)
  • 4 ounces cream cheese, softened (for frosting)
  • 1/2 cup powdered sugar (for frosting)
  • 1/4 cup unsweetened cocoa powder (for frosting)
  • 1 teaspoon vanilla extract (for frosting)
  • 2 tablespoons milk (for frosting, adjust as needed)

Instructions

  1. Activate the yeast: In a large bowl, combine the warm milk, yeast, and 1 tablespoon of the granulated sugar. Let stand for 5 to 10 minutes until foamy.
  2. Prepare the dough: Add the remaining granulated sugar, melted butter, egg, 3 cups of flour, and 1/2 cup cocoa powder to the yeast mixture. Mix until a shaggy dough forms. Knead on a lightly floured surface for 6 to 8 minutes until smooth and elastic. Add up to 1/2 cup more flour if the dough is too sticky.
  3. First rise: Place the dough in a lightly oiled bowl, turning to coat. Cover and let rise in a warm place for 1 to 1.5 hours, or until doubled in size.
  4. Make the filling: While the dough rises, mix the softened butter, brown sugar, cinnamon, and chocolate chips in a small bowl until combined. Set aside.
  5. Roll out the dough: Punch down the risen dough and turn it out onto a lightly floured surface. Roll the dough into a large rectangle, about 12 by 18 inches.
  6. Spread the filling: Spread the chocolate filling evenly over the dough, leaving a 1-inch border on one long edge.
  7. Shape the rolls: Starting from the long edge opposite the border, tightly roll the dough into a log. Pinch the seam closed.
  8. Cut the rolls: Cut the log into 12 equal pieces. Place the rolls cut-side up in a greased 9×13 inch baking dish.
  9. Second rise: Cover the dish and let the rolls rise again in a warm place for 30 to 45 minutes, until puffy.
  10. Bake the rolls: Preheat your oven to 375°F. Bake for 20 to 25 minutes, until the tops are set.
  11. Make the frosting: While the rolls cool slightly, beat the softened cream cheese, powdered sugar, 1/4 cup cocoa powder, and vanilla extract until smooth. Add milk one tablespoon at a time until you reach a thick, spreadable consistency.
  12. Frost and serve: Spread the chocolate cream cheese frosting generously over the warm rolls. Serve immediately for a molten center experience.

Notes

  • For extra gooey chocolate rolls, press a few extra chocolate chips into the top of each roll before the second rise.
  • If you prefer a thinner glaze, reduce the powdered sugar in the frosting recipe or add more milk.
  • You can prepare the dough the night before, place it in the refrigerator after the first rise, and let it finish rising at room temperature the next morning.

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