Triple Chocolate Cinnamon Rolls are a decadent twist on classic cinnamon rolls, featuring rich chocolate dough, a gooey chocolate-cinnamon filling, and a luxurious chocolate glaze. These impressive pastries combine the beloved swirls and fluffy texture of traditional cinnamon rolls with deep, intense chocolate flavor in every layer. The dough is enriched with cocoa powder, the filling features chocolate chips and cinnamon-chocolate spread, and the glaze is pure chocolate heaven. Perfect for special breakfasts, brunch gatherings, Valentine’s Day, or anytime you want to impress chocolate lovers, these rolls prove that breakfast can be dessert. They’re as beautiful as they are delicious, with chocolate swirls visible in every slice and a glossy chocolate topping that makes them irresistible.
Serving Quantity: 12 cinnamon rolls
Preparation Time: 30 minutes
Cooking Time: 25 minutes
Total Time: 3 hours 30 minutes (including rising time)
Ingredients:
For the Dough:
- 3 and a half cups all-purpose flour
- Half cup unsweetened cocoa powder
- Quarter cup granulated sugar
- 1 packet (2 and a quarter teaspoons) instant yeast
- 1 teaspoon salt
- 1 cup whole milk (warmed to 110°F)
- Quarter cup unsalted butter (melted)
- 2 large eggs
- 1 teaspoon vanilla extract
For the Filling:
- Half cup unsalted butter (softened)
- Three-quarters cup packed brown sugar
- Quarter cup unsweetened cocoa powder
- 2 teaspoons ground cinnamon
- 1 cup semi-sweet chocolate chips
- Pinch of salt
For the Chocolate Glaze:
- 1 and a half cups powdered sugar
- Quarter cup unsweetened cocoa powder
- Quarter cup unsalted butter (melted)
- 3 to 4 tablespoons heavy cream
- 1 teaspoon vanilla extract
- Pinch of salt
Nutrition Information (Per Roll):
- Calories: 485
- Protein: 8g
- Carbohydrates: 72g
- Fat: 20g
- Sugar: 42g
- Sodium: 245mg
- Fiber: 4g
- Cholesterol: 65mg
1. Make the Chocolate Dough
In the bowl of a stand mixer fitted with the dough hook, combine the flour, cocoa powder, granulated sugar, instant yeast, and salt. Mix briefly on low speed to combine the dry ingredients. In a separate bowl, whisk together the warm milk, melted butter, eggs, and vanilla extract. The milk should be warm but not hot, around 110 degrees Fahrenheit. Pour the wet ingredients into the dry ingredients. Mix on low speed until a shaggy dough forms, then increase to medium speed and knead for 6 to 8 minutes until the dough is smooth, elastic, and slightly tacky but not sticky. The dough will be darker than regular cinnamon roll dough due to the cocoa.
2. First Rise
Shape the dough into a ball and place it in a greased bowl, turning once to coat all sides. Cover with plastic wrap or a damp kitchen towel. Let rise in a warm, draft-free place for 1 to 1 and a half hours until doubled in size. The dough should feel puffy and when you press a finger into it, the indentation should remain. A warm oven that’s been turned on briefly then turned off works well as a proofing spot. This first rise develops flavor and creates the fluffy texture.
3. Prepare the Chocolate Filling
While the dough rises, make the filling. In a medium bowl, mix together the softened butter, brown sugar, cocoa powder, ground cinnamon, and a pinch of salt until smooth and spreadable. The mixture should be like a thick paste. If it’s too stiff, let it sit at room temperature to soften. If too soft, refrigerate briefly. The combination of chocolate and cinnamon creates a uniquely delicious flavor that’s warming and indulgent. Set aside until ready to use.
4. Roll and Fill
Once the dough has doubled, punch it down to release the gas. Turn it out onto a lightly floured surface and roll into a large rectangle, approximately 12 by 18 inches and about a quarter inch thick. Spread the chocolate-cinnamon filling evenly over the entire surface, leaving a half-inch border along one long edge. Sprinkle the chocolate chips evenly over the filling. The chips will melt during baking, creating pockets of gooey chocolate throughout the rolls.
5. Roll and Cut
Starting from the long edge with filling (not the clean border), tightly roll the dough into a log, rolling away from you. The tighter you roll, the more defined your swirls will be. When you reach the clean edge, pinch it closed to seal the seam. Position the log seam-side down. Using a sharp knife or unflavored dental floss, cut the log into 12 equal pieces, each about one and a half inches thick. Dental floss creates cleaner cuts without squishing the dough. Grease a 9 by 13 inch baking pan. Arrange the rolls cut-side up in the pan in a 3 by 4 grid.
6. Second Rise and Bake
Cover the pan loosely with plastic wrap or a kitchen towel. Let the rolls rise for 30 to 45 minutes until puffy and nearly doubled. They should be touching each other and look pillowy. Meanwhile, preheat your oven to 350 degrees Fahrenheit. Once risen, remove the covering and bake for 23 to 27 minutes until the rolls are set and a toothpick inserted in the center comes out clean with just a few moist crumbs. The chocolate chips will be melted and bubbling. Don’t overbake or they’ll be dry. Remove from the oven and let cool in the pan for 10 minutes.
7. Make the Glaze and Serve
While the rolls cool slightly, make the chocolate glaze. In a medium bowl, whisk together the powdered sugar and cocoa powder. Add the melted butter, 3 tablespoons of heavy cream, vanilla extract, and a pinch of salt. Whisk until smooth and glossy. The glaze should be thick but pourable. If too thick, add more cream a teaspoon at a time. If too thin, add more powdered sugar. Drizzle or spread the glaze generously over the warm rolls. The glaze will melt slightly and seep into the crevices. Serve warm for the ultimate gooey, chocolatey experience.
Tips for Perfect Triple Chocolate Cinnamon Rolls
Use Dutch-process cocoa powder for the deepest, richest chocolate flavor and darker color. Natural cocoa works but won’t be as intensely chocolate.
Don’t skip the first rise even though it takes time. This develops flavor and creates the fluffy, tender texture that makes cinnamon rolls special.
The dough should be slightly tacky after kneading, not sticky. If it’s too sticky, add flour a tablespoon at a time. If too dry, add milk a teaspoon at a time.
Warm the milk to exactly 110 degrees Fahrenheit. Too hot kills the yeast, too cold won’t activate it properly. Use a thermometer for accuracy.
Roll the dough tightly for well-defined swirls. Loose rolling creates gaps and the filling can leak out during baking.
Use dental floss for the cleanest cuts. Place it under the log, cross the ends over the top, and pull tight to slice through without squishing.
Don’t overbake. The rolls should be set but still soft. They firm up as they cool. Overbaking creates dry, tough rolls.
Make ahead by assembling the rolls the night before. Cover tightly and refrigerate overnight. Let come to room temperature for 30 minutes, then bake as directed.
These freeze beautifully before or after baking. Freeze unbaked rolls in the pan, tightly wrapped, for up to 3 months. Bake from frozen, adding 10 minutes to baking time.
The glaze can be made while the rolls bake to save time. Rewarm gently if it thickens too much before serving.
Add espresso powder to the dough, filling, or glaze for mocha-flavored rolls. One to two teaspoons amplifies the chocolate flavor beautifully.
Mini chocolate chips distribute more evenly than regular chips. They create more pockets of melted chocolate throughout rather than occasional large chunks.
Different chocolates create different flavors. Try dark chocolate chips for intense flavor or milk chocolate for sweeter, creamier results.
Serve with vanilla ice cream for an over-the-top dessert. The contrast of cold ice cream with warm chocolate rolls is incredible.
Store leftovers covered at room temperature for up to 2 days or refrigerated for up to 5 days. Reheat individual rolls in the microwave for 20 to 30 seconds.
Add a tablespoon of orange zest to the filling for chocolate-orange rolls. The citrus complements chocolate beautifully and adds sophistication.
Make the glaze thicker for spreading or thinner for drizzling based on your preference. Adjust the cream amount to achieve desired consistency.
These make stunning holiday gifts. Bake in disposable aluminum pans, let cool, wrap well, and give with reheating instructions.
Add chopped nuts like pecans or walnuts to the filling for crunch. Toast them first for maximum flavor and distribute evenly with the chocolate chips.
The rolls are best served warm when the chocolate is gooey and the glaze is melty. Reheat before serving for the ultimate experience.
