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Decadent Chocolate Cinnamon Rolls with Gooey Chocolate Filling

Two gooey chocolate cinnamon rolls stacked, showing the soft interior and thick chocolate frosting.

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Make these rich chocolate cinnamon rolls featuring a soft cocoa brioche dough, a luscious cinnamon chocolate swirl filling, and a decadent chocolate cream cheese frosting. This recipe delivers the ultimate gooey texture perfect for brunch or dessert.

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 teaspoon salt
  • 1/2 cup unsweetened cocoa powder
  • 1/2 cup (1 stick) unsalted butter, softened (for filling)
  • 1/2 cup packed light brown sugar (for filling)
  • 2 tablespoons ground cinnamon (for filling)
  • 4 ounces semi-sweet chocolate, finely chopped (for filling)
  • 1/2 cup cream cheese, softened (for frosting)
  • 2 cups powdered sugar, sifted (for frosting)
  • 1/4 cup unsweetened cocoa powder (for frosting)
  • 24 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, melted butter, and vanilla extract to the yeast mixture. Whisk briefly.
  3. Combine dry ingredients: In a separate bowl, whisk together the flour, salt, and 1/2 cup cocoa powder. Gradually add the dry mixture to the wet ingredients, mixing until a shaggy dough forms.
  4. Knead the dough: Turn the dough out onto a lightly floured surface and knead for 6 to 8 minutes until 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.
  5. Prepare the filling: While the dough rises, mix the softened butter, brown sugar, 2 tablespoons of cinnamon, and chopped chocolate in a small bowl until combined.
  6. Shape the rolls: Punch down the risen dough. Roll it out on a lightly floured surface into a 12×18 inch rectangle. Spread the chocolate filling evenly over the dough, leaving a 1-inch border on one long edge.
  7. Roll and cut: Tightly roll the dough up starting from the long edge opposite the border. Pinch the seam to seal. Cut the log into 12 equal pieces.
  8. Second rise: Place the rolls cut-side up in a greased 9×13 inch baking dish. Cover and let them rise again for 30 to 45 minutes until puffy.
  9. Bake the rolls: 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 beat in the powdered sugar and 1/4 cup cocoa powder. Add milk one tablespoon at a time until you reach a smooth, spreadable consistency for your chocolate cream cheese frosting.
  11. Frost and serve: Spread the warm rolls generously with the chocolate cream cheese frosting. Serve immediately for the best gooey texture.

Notes

  • For extra gooey chocolate cinnamon rolls, let the dough proof in a slightly warmer spot.
  • If you prefer a thinner topping, make a simple chocolate glaze using powdered sugar, cocoa powder, and a splash of hot water or coffee instead of the cream cheese frosting.
  • You can prepare the dough the night before, place the cut rolls in the pan, cover, and refrigerate overnight. Add 15 minutes to the second rise time before baking.

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