The best chocolate cinnamon rolls! A chocolatey cinnamon sugar filling is swirled inside a chocolate cinnamon roll dough and topped with an irresistible chocolate cream cheese frosting.
Combine water, 1 Tablespoon sugar and yeast in the bowl of a standing mixer fitted with the dough hook. Stir and let sit until foamy (5-10 minutes). (Alternately, you can mix the dough by hand with a wooden spoon in a large bowl).
Add milk, ¼ cup sugar, melted butter, egg, and vanilla to the mixture in the bowl of your standing mixer. Use a dough hook to stir until combined.
Add 2 cups flour, salt, cinnamon and cocoa powder and stir with the dough hook, starting on low and increasing to high.
Add more flour, ¼ cup at a time until a smooth ball is formed. The dough should be smooth and only slightly tacky to the touch.
Transfer dough to a floured surface and knead with your hands until it is smooth and elastic (about 3-5 minutes). Form it into a ball.
Grease a large bowl and place the dough inside.
Cover the bowl with a warm, damp towel and put the bowl in a warm place to rise for 1 hour or until dough has doubled in size.
Make the Filling
While the dough is rising, make the filing. Combine the cinnamon and sugar in a small bowl. Then melt the butter and set aside (It will be brushed on the dough later).
Alternately, you can combine butter, brown sugar, cinnamon until mixture is homogenous (uniform throughout). Set aside.
Assemble
Sprinkle a large work surface with flour.
Gently press the gas out of the dough and form it into a rectangle.
Roll the dough into a rectangle that’s 18” long and 10” wide (18x10”), and about ¼ inch thick.
Either: 1) Use a pastry brush to spread the melted butter all over the dough. Then sprinkle the dough with cinnamon sugar mixture and pat it down gently to insure it sticks. Or 2) Spread the filling over the dough using greased hands or a greased spatula. This process can seem difficult, but it gets easier as you spread it.
Spread the chocolate chips evenly over the cinnamon sugar mixture.
Tightly roll the dough and cut into 9 equal sized rolls (I recommend measuring by placing a tape measure next to the rolled dough to ensure it’s 18” long, then make marks every 2 inches and cut the rolls to be 2” wide).
Line an 8x8” or 9x9” baking dish with parchment paper and lightly grease. Then place rolls in 3 rows of 3, evenly spaced.
Cover and let rise until nearly doubled, or slightly puffed about 30-60 minutes (the rolls will rise more while they are baking).
Bake
Preheat oven to 350 degrees Fahrenheit.
Once rolls are risen, bake them in the preheated oven until golden brown, about 25-30 minutes. They will rise more in the oven.
Make the Chocolate Cream Cheese Frosting
While rolls are baking, beat together cream cheese, butter, powdered sugar, cocoa powder, vanilla extract and salt until smooth. Do not chill the frosting. Keep it at room temperature until the cinnamon rolls are baked.
Once the cinnamon rolls have been removed from the oven, spread the cream cheese frosting on them while they are still warm.
Let cool slightly and serve warm.
Video
Notes
Nutritional information calculated for just the rolls without frosting. Tip: When done flip over onto a baking sheet and let juices go back into rolls.Ingredient Substitutions
WholeMilk. half and half or 2% milk are good substitutes - I don't recommend anything with a lower fat content.
All-purpose flour. bread flour may be used in place of all-purpose flour.
Unsweetened cocoa powder. dark cocoa powder can be used to make these extra chocolatey.
Salted butter. Unsalted butter or ghee are both good substitutes for salted butter.
Light brown sugar. for a richer molasses taste, use dark brown sugar.
Ground Cinnamon. The quality of cinnamon used in this recipe really matters. Please choose your cinnamon wisely!
Mini chocolate chips. I like using mini chips because they distribute throughout the dough very well. You can use full-size chips or chopped chocolate, if preferred.
Cream cheese. Full fat or light cream cheese both work well in this recipe. The higher the fat content, the richer the taste.
Vanilla extract. Vanilla bean paste is a good substitute for extract.
StoreStore leftover cinnamon rolls in an airtight container in the refrigerator for up to 5 days. Reheat in the microwave.How to make chocolate cinnamon rolls in advance
Make the recipe according to the recipe instructions all the way up until you cut the rolls and put them in the baking sheet.
Tightly wrap the assembled, but not risen, cinnamon rolls with plastic wrap and cover with a damp tea towel or the lid to the baking dish.
Refrigerate overnight.
In the morning, remove the assembled rolls from the refrigerator. Loosen the plastic wrap and let the cinnamon rolls come to room temperature and complete their second rise covered with loose-fitting plastic wrap and a warm, damp tea towel.
Bake risen rolls according to the recipe!
You can also make the frosting in advance and store it in the refrigerator. Remove it from the refrigerator when you take the rolls out to rise so it can come to room temperature before spreading it on the warm rolls.To Freeze Cinnamon Roll Dough:Once the rolls are assembled in the baking dish before baking – tightly wrap them with plastic wrap and cover them with tinfoil. Then freeze for up to 1 month before baking. To bake cinnamon rolls after the dough has been frozen:
Remove the frozen cinnamon roll dough from the freezer the night before you would like to bake them.
Leave the dough on the counter to come to room temperature and rise until doubled in size or slightly puffed (they will rise more while baking).
After the dough has risen, bake and frost according to the recipe instructions.
To freeze baked cinnamon rolls:Let the rolls cool and freeze them (either frosted or unfrosted) in an airtight container for up to 2 months. Let thaw in the refrigerator and warm in the microwave or oven.