If regular homemade cinnamon rolls were married to semisweet chocolate, you'd get these gooey and over-the-top pastries with chocolate in the filling and topping. A double dose, just in case. The dough can be made ahead, and the baked rolls can be frozen; another reason to make these often.
Combine 2 ¼ cups cake flour, 2 ¼ cups all-purpose or bread flour, ½ cup sugar and 2 ¼ teaspoons dry yeast in the bowl of a stand mixer. If making them by hand, use a large mixing bowl.
Add ¾ cup milk, 3 eggs, 6 tablespoons unsalted butter, melted, and 1 teaspoon salt.
Attach the dough hook and knead at medium-low speed for 1 or 2 minutes. Increase to medium speed and knead for 7-8 minutes more or until a dough forms. It will not separate completely from the bowl, and it will be barely sticky. If it’s too sticky add a few tablespoons of flour, one at a time, but not too many, kneading for about 30 seconds before deciding if it needs more. The dough will become supple after the first rise, so be careful with the extra flour.
Transfer this dough to an oiled bowl, turn it over to coat it fully, cover the bowl with plastic wrap or a clean towel and let rise in a draft-free area until doubled in volume, about 2 hours. Have the filling ingredients ready before rolling the dough.
Meanwhile, preheat the oven to 350ºF (180ºC) about half an hour before baking.
Gently turn the dough onto a clean counter and pat into a rectangle, about 16x12 inches (30x40cm), the long side parallel to the counter.
For the filling:
Pat mounds with 1 cup unsalted butter, softened, all over the dough. Gently spread it to cover the entire surface. Be careful not to tear the dough.
Mix 1 cup light brown sugar, 1 teaspoon ground cinnamon and 2 tablespoons unsweetened cocoa powder in a small bowl. Sprinkle it on top of the butter. Sprinkle ½ cup semisweet chocolate chips.
Lift the longest edge closer to you, from one end to the other, and keep rolling, trying to tighten it as you do.
Use a large kitchen knife to cut it into 12 pieces. Start by cutting the dough in half, then each piece in thirds to make six pieces, and each piece in half again.
Place in a greased or buttered 9x13-inch baking dish, cover with a clean towel, and let it rise for 1 hour or until puffed.
Bake for 20 to 25 minutes until golden, puffed, and baked through.
Prepare the glaze:
Mix 2 tablespoons unsweetened cocoa powder with ½ cup powdered sugar2 tablespoons whole milk or heavy cream and ½ teaspoon vanilla extract until smooth.
Drizzle over warm rolls and let dry before eating.
Notes
Baking time: Keep in mind that all ovens and pans can vary, even if they appear similar. The baking time in my recipes is as accurate as possible, but it might take you more or less time. You can use an oven thermometer to check that your oven is at the right temperature. I recommend tracking how your oven works, identifying any small details you might need to adjust. Freezing and reheating the rolls: If making them in advance, freeze them without the glaze. Use a freezer-safe airtight bag or cover in plastic wrap and then aluminum foil. Thaw the frozen rolls in the refrigerator overnight. When ready to eat, reheat them in the oven at a low temperature (around 300°F or 150°C) for 5-10 minutes. If freezing glazed leftovers, be careful that the chocolate glaze doesn't get too drippy when reheating them.