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Triple Chocolate Cinnamon Rolls with Gooey Glaze

Close-up of gooey chocolate cinnamon rolls stacked on a white plate, dripping with thick chocolate glaze.

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Make soft, fluffy chocolate cinnamon rolls at home. This recipe features a rich chocolate dough, a decadent chocolate-cinnamon filling, and a luscious chocolate cream cheese frosting for a truly satisfying treat.

Ingredients

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

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. Mix the dough: Add the remaining granulated sugar, egg, and melted butter to the yeast mixture. Stir well. In a separate bowl, whisk together the flour, cocoa powder, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until a shaggy dough forms.
  3. Knead: Turn the dough out onto a lightly floured surface. Knead for 6 to 8 minutes until the dough is smooth and elastic. Place the dough in a lightly oiled bowl, cover it, and let it rise in a warm place for 1 to 1.5 hours, or until doubled in size.
  4. Prepare the filling: While the dough rises, mix the softened butter, brown sugar, cinnamon, and chocolate chips in a small bowl until combined. This creates your chocolate-cinnamon filling.
  5. Roll out the dough: Punch down the risen dough. On a lightly floured surface, roll the dough into a large rectangle, about 12 by 18 inches.
  6. Fill and shape: Spread the chocolate filling evenly over the dough, leaving a small border on one long edge. Sprinkle any extra chocolate chips over the filling. Roll the dough tightly starting from the long edge opposite the border. Pinch the seam closed.
  7. Cut the rolls: Slice the log into 12 equal pieces, about 1.5 inches thick. Place the rolls cut-side up in a greased 9×13 inch baking dish.
  8. Second rise: Cover the dish loosely and let the rolls rise again in a warm spot for 30 to 45 minutes, until puffy.
  9. Bake: Preheat your oven to 375°F (190°C). Bake for 20 to 25 minutes, or until the tops are set and cooked through.
  10. Make the frosting: While the rolls cool slightly, beat the softened cream cheese until smooth. Gradually add the powdered sugar and milk until you reach a smooth, spreadable consistency.
  11. Glaze and serve: Drizzle the chocolate cream cheese frosting generously over the warm rolls. Serve immediately for the best gooey texture.

Notes

  • For a richer chocolate flavor in the dough, substitute 1/4 cup of the flour with an equal amount of Dutch-processed cocoa powder.
  • If you prefer a hot cocoa cinnamon roll variation, fold 1/2 cup of mini marshmallows into the filling mixture before spreading it on the dough.
  • To achieve bakery-style soft rolls, cover the pan with foil for the first 10 minutes of baking, then remove the foil to brown the tops.

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