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Gooey Triple Chocolate Cinnamon Rolls with Chocolate Cream Cheese Frosting

Close-up of a fluffy chocolate cinnamon roll generously covered in thick, glossy chocolate glaze.

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Make soft, decadent chocolate cinnamon rolls featuring a rich chocolate dough, a gooey chocolate filling, and a smooth chocolate cream cheese frosting.

Ingredients

Scale
  • 1 cup whole milk, warmed
  • 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
  • 1/4 cup unsweetened cocoa powder
  • 1 teaspoon salt
  • 1/2 cup unsalted butter, softened (for filling)
  • 1 cup packed light brown sugar (for filling)
  • 1/4 cup unsweetened cocoa powder (for filling)
  • 1 teaspoon ground cinnamon (for filling)
  • 4 ounces bittersweet chocolate, finely chopped (for filling)
  • 8 ounces cream cheese, softened (for frosting)
  • 1/2 cup unsalted butter, softened (for frosting)
  • 2 cups powdered sugar (for frosting)
  • 1/2 cup unsweetened cocoa powder (for frosting)
  • 1 teaspoon vanilla extract (for frosting)
  • 2-4 tablespoons milk (for frosting)

Instructions

  1. Combine the warm milk, yeast, and 1 teaspoon of the sugar in a bowl. Let stand for 5 minutes until foamy.
  2. In a large bowl, whisk together the flour, 1/2 cup cocoa powder, and salt.
  3. Add the melted butter, remaining sugar, and egg to the yeast mixture. Mix well.
  4. Gradually add the wet ingredients to the dry ingredients, mixing until a shaggy dough forms. Knead on a lightly floured surface for 6-8 minutes until smooth.
  5. Place the dough in a lightly oiled bowl, cover, and let rise in a warm place for 1 to 1.5 hours, or until doubled.
  6. While the dough rises, prepare the filling: In a bowl, mix the softened butter, brown sugar, 1/4 cup cocoa powder, and cinnamon until smooth. Stir in the chopped bittersweet chocolate.
  7. Punch down the risen dough. Roll it out on a lightly floured surface into a 12×18 inch rectangle.
  8. Spread the chocolate filling evenly over the dough, leaving a 1-inch border on one long edge.
  9. Tightly roll the dough starting from the long edge opposite the border. Pinch the seam closed.
  10. Cut the log into 12 equal rolls. Place them in a greased 9×13 inch baking pan. Cover and let rise for 30 minutes.
  11. Preheat your oven to 375 degrees Fahrenheit. Bake for 20-25 minutes until cooked through.
  12. While the rolls bake, prepare the frosting: Beat the cream cheese and butter until smooth. Gradually add the powdered sugar and 1/2 cup cocoa powder. Mix in the vanilla and 2 tablespoons of milk. Add more milk if needed for a spreadable consistency.
  13. Remove rolls from the oven and immediately spread the chocolate cream cheese frosting over the warm rolls. Serve warm.

Notes

  • For an extra gooey texture, you can add 1/2 cup of mini marshmallows into the filling before rolling.
  • If you prefer a thinner glaze instead of thick frosting, reduce the powdered sugar in the frosting recipe by half and increase the milk to 1/4 cup.
  • If you want to make these ahead, assemble the rolls, cover them tightly, and refrigerate overnight. In the morning, let them sit at room temperature for 30 minutes before baking, adding 5-10 minutes to the bake time.

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