All of the goodness of a classic cinnamon roll but filled with delicious bits of chocolate and topped with a sweet chocolate icing! These chocolate cinnamons rolls are a chocolate lover's dream!
In a small bowl , stir together the warm milk, yeast, and 1 Tablespoon sugar. Let sit about 5 minutes, or until bubbly.
In a large bowl, whisk the egg. Beat in the remaining 7 Tablespoons sugar and salt. Stir in the melted butter and the yeast mixture. Add 2 cups flour and stir until smooth. Add the remaining flour, 1/2 cup at a time. Knead 4 to 5 minutes, or until the dough is smooth and soft. If the dough is too sticky, add 1 to 2 Tablespoons flour.
Cover the bowl with a towel or plastic wrap and place in a warm spot for about an hour (see notes). Once dough has doubled in size, punch it down.
Chocolate Filling
Butter or spray a 9x13-inch glass baking dish with nonstick spray.
In a small bowl, mix together the butter, brown sugar, cinnamon, and cocoa powder.
On a floured surface, roll out the dough into a rectangle, approximately 15x20 inches. It doesn’t have to be perfect. Spread butter mixture onto the dough with a pastry brush.
Sprinkle the chopped chocolate over top. Gently press down into the butter. Roll the dough up tightly starting at the shorter side. Pinch the sides together at the end.
Using floss or a large serrated knife, cut the dough in half and cut each half into 6 (1-inch pieces) for a total of 12 rolls. Place rolls in baking dish, about 1-inch apart. Cover with a towel and let the rolls sit 1 hour, or until rolls have doubled in size.
Preheat the oven to 350°F.
Bake 25 to 30 minutes, or until lightly golden brown on top. Remove from oven and let cool 20 to 30 minutes before frosting.
Chocolate Icing
In a large bowl, whisk together the powdered sugar, cocoa, milk, butter, vanilla, and a pinch of salt. Mix until well combined. You can add more milk or powdered sugar to reach your desired consistency. It should fall like a ribbon from the spoon.
Drizzle the icing over the slightly cooled cinnamon rolls.
Notes
Rising tip: Turn the oven to 175°F. Once preheated, turn off the oven and place the dough inside to rise. Make ahead: Before the 2nd rise, cover the pan tightly with plastic wrap and then place in the refrigerator for up to 16 hours. Then the next morning, pull them out onto the counter and let them rise until doubled, about 1 to 2 hours. It is normal for there to be a little liquid, but if there's too much, get a paper towel and dab it out. Freezing the cinnamon rolls: You can freeze the chocolate cinnamon rolls after they have been baked and cooled. Simply place in a freezer container or zip-top bag. Place in refrigerator to thaw overnight. Warm individual rolls in microwave for 10 to 20 seconds.