Double Chocolate Cinnamon Rolls

The first time I made these double chocolate cinnamon rolls, it was a snowed-in Sunday morning and my roommate kept wandering into the kitchen asking if they were done yet. The combination of cocoa in the dough and that chocolate-cinnamon filling makes the whole house smell like a bakery crossed with a chocolate shop.

Last Christmas morning I made a double batch because my family had requested them specifically. We ended up eating them straight from the pan with our hands, burning our fingers slightly and not caring one bit.

Ingredients

• 3 1/2 cups all-purpose flour: Forms the structure of the dough, and measuring accurately makes all the difference between fluffy and dense rolls
• 1/4 cup unsweetened cocoa powder: Dont skip this, it gives the dough its deep chocolate flavor and keeps the crumb tender
• 1 packet instant yeast: Instant yeast cuts down on prep time since you can mix it directly with the dry ingredients
• 1/3 cup granulated sugar: Feeds the yeast and adds subtle sweetness to the dough itself
• 1/2 tsp salt: Crucial for balancing all the chocolate sweetness and bringing out the cocoa flavors
• 1 cup whole milk, warm: Warm to about 110°F, it activates the yeast without killing it
• 1/4 cup unsalted butter, melted: Adds richness and helps create that tender crumb structure
• 1 large egg, room temperature: Bring it to room temp so it incorporates evenly into the dough
• 1/2 cup brown sugar, packed: The molasses in brown sugar creates a caramel-like quality as it bakes
• 1/4 cup unsweetened cocoa powder: Pairs with cinnamon for that mocha-like filling flavor
• 1 1/2 tsp ground cinnamon: The classic cinnamon roll spice that marries surprisingly well with chocolate
• 1/4 cup unsalted butter, softened: Soft butter spreads evenly without tearing the dough
• 1/2 cup dark chocolate chips: Dark chocolate holds its shape better during baking and cuts through the sweetness
• 1 cup powdered sugar: Creates the smooth base for the glaze
• 1/4 cup unsweetened cocoa powder: Makes this a truly double chocolate experience
• 2 to 3 tbsp whole milk: Adjust this to get your desired glaze consistency
• 1/2 tsp vanilla extract: Enhances all the chocolate flavors

Instructions

Mix your dry ingredients:

In a large bowl whisk together the flour, cocoa powder, yeast, sugar, and salt until everything is evenly combined

Combine the wet mixture:

Pour in the warm milk, melted butter, and egg, stirring until a sticky shaggy dough forms

Knead until smooth:

Knead by hand or with a stand mixer for 8 to 10 minutes until the dough feels smooth and elastic, bouncing back when you poke it

Let it rise:

Place dough in a greased bowl, cover, and let rise in a warm spot until doubled, about 1 hour

Roll out the dough:

Punch down the risen dough and roll on a floured surface into a 16x12-inch rectangle

Spread the butter:

Spread the softened butter evenly over the entire surface of the dough

Mix the filling:

Stir together the brown sugar, cocoa powder, and cinnamon in a small bowl

Add the filling:

Sprinkle the sugar mixture evenly over the buttered dough, then scatter chocolate chips on top

Roll and slice:

Starting from a long edge, roll the dough tightly into a log and cut into 12 equal rolls

Second rise:

Arrange rolls in a greased 9x13-inch baking dish, cover, and let rise until puffy, 30 to 45 minutes

Bake to perfection:

Preheat oven to 350°F and bake for 22 to 25 minutes until set and lightly browned

Make the glaze:

While rolls cool slightly, whisk together powdered sugar, cocoa powder, milk, and vanilla

Finish and serve:

Drizzle the chocolate glaze generously over the warm rolls before serving

Save Pin

My neighbor texted me the next day asking what I had made because the smell had drifted through the building vents. Now whenever I make them, I double the recipe and bring a pan upstairs.

Make Ahead Magic

You can assemble these rolls the night before, refrigerate after placing them in the baking dish, then let them rise at room temperature for about an hour before baking. This makes weekend mornings so much more manageable.

Getting That Perfect Swirl

If your dough keeps springing back when you roll it, let it rest for 5 minutes and try again. Use unflavored dental floss or a sharp serrated knife to cut the rolls, pressing straight down instead of sawing.

Serving Ideas

Serve these warm from the oven with a cup of strong coffee or cold glass of milk. For an over-the-top dessert, add a scoop of vanilla ice cream to a warm roll and let the ice cream melt into all the chocolate pockets.

• Fresh raspberries or strawberries cut through the richness beautifully
• A sprinkle of sea salt on the glaze makes the chocolate pop
• Leftovers reheat beautifully in the microwave for 20 seconds

Save Pin

These double chocolate cinnamon rolls have become my go-to for special occasions, snow days, and anytime chocolate cravings strike at breakfast.

Recipe FAQs

→ Can I make these the night before?

Yes. Complete through step 10, placing the sliced rolls in your baking dish. Cover tightly and refrigerate overnight. In the morning, let them sit at room temperature for about an hour until puffy, then bake as directed. The cold rise actually develops deeper flavor.

→ What type of chocolate works best for the filling?

Dark chocolate chips or chopped dark chocolate (60-70% cocoa) creates the best balance. The slight bitterness cuts through the sweet brown sugar and complements the cinnamon. Semi-sweet works too, but avoid milk chocolate as it can make the filling overly sweet and may seize during baking.

→ Why add cocoa powder to the dough?

Cocoa powder in the dough creates a chocolate base that carries through every layer, not just the filling. It also gives the rolls a beautiful deep color and subtle chocolate undertone that enhances the overall flavor profile without being overpowering.

→ How do I know when the rolls are done baking?

The rolls are finished when they're set and lightly golden brown on top, about 22-25 minutes at 350°F. You can also insert a thermometer into the center roll—it should read 190-200°F. Avoid overbaking, which can dry them out. They'll continue cooking slightly from residual heat.

→ Can I freeze these before or after baking?

Both methods work. For freezing unbaked: complete through step 10, wrap the baking dish tightly, and freeze for up to 2 weeks. Thaw overnight in the refrigerator, then let rise at room temperature before baking. For freezing baked: cool completely, wrap individually, and freeze for up to 1 month. Reheat in the microwave or oven.

→ My dough is too sticky to handle. What should I do?

Chocolate dough tends to be stickier than plain dough due to cocoa powder's moisture absorption. Lightly flour your hands and work surface, but avoid adding too much flour to the dough itself or the rolls will become tough. If necessary, chill the dough for 15-20 minutes to make it easier to roll out.