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Sinful Chocolate Cinnamon Rolls

Soft, fluffy, chocolate infused cinnamon rolls filled with rich chocolate cinnamon sugar, baked with cream for extra gooey centers, and finished with a luscious chocolate cream cheese frosting. An indulgent treat perfect for brunch, dessert, or special mornings.
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Course: Breakfast
Cuisine: American
Keyword: chocolate cinnamon rolls, chocolate cream cheese cinnamon rolls, chocolate filled cinnamon rolls, chocolate swirled cinnamon rolls, double chocolate cinnamon rolls, homemade cinnamon rolls, soft and fluffy cinnamon rolls
Prep Time: 25 minutes
Cook Time: 40 minutes
Rise Time: 3 hours
Total Time: 4 hours 5 minutes
Servings: 10 rolls

Ingredients

Dough

  • 1¼ cup buttermilk
  • 2 ½ tsp instant dry yeast
  • 6 tbsp unsalted butter softened
  • 2 large eggs
  • 2/3 cup granulated sugar
  • 1 tsp salt
  • 4 cups all-purpose flour
  • ¼ cup cocoa powder
  • 2 tbsp hot coffee

Chocolate Cinnamon Filling

  • 1 cup light brown sugar
  • 3 tbsp cinnamon
  • 1 tbsp cocoa powder
  • 6 tbsp unsalted butter softened
  • 1 tsp espresso powder
  • ½ c. mini chocolate chips

Before Baking

  • 2/3 cup heavy cream poured on the bottom of the baking pan

Chocolate Cream Cheese Frosting

  • 4 oz cream cheese softened
  • 5 tbsp unsalted butter softened
  • 1 tsp vanilla extract
  • 1½ cups powdered sugar
  • 2 tbsp cocoa powder
  • Pinch of salt
  • 2 oz dark chocolate melted, slightly cooled
  • 2 –3 tbsp heavy cream

Instructions

Make the dough:

  • In a stand mixer fitted with the dough hook, combine softened butter, eggs, granulated sugar, salt, flour, cocoa powder, buttermilk, yeast, and hot coffee. Mix until roughly combined and then knead on medium speed for 4–5 minutes, until smooth and elastic. Cover and let rise 1½ -2 hours, until doubled.

Prepare the filling:

  • Mix brown sugar, cinnamon, cocoa powder, chocolate chips, and espresso powder in a small bowl. Keep 6 tbsp butter ready for spreading.

Shape the rolls:

  • Lightly flour a work surface and roll the dough into a 12×18” rectangle. Spread the softened butter over the dough, then sprinkle the cinnamon sugar mixture evenly. Starting at the long side, roll the dough into a tight log.

Cut rolls:

  • Cut the log into 10 equal pieces and place them in a greased 9×13” baking pan.

Second rise:

  • Cover the pan and let the rolls rise another hour, or refrigerate overnight.

Preheat oven:

  • Preheat to 350°F (175°C). If refrigerated, remove rolls from fridge while oven preheats.

Pour cream:

  • Just before baking, pour 2/3 cup heavy cream evenly into the bottom of the pan (not over the tops). This keeps rolls extra gooey.

Bake:

  • Bake 40–45 minutes until golden and center is cooked through.

Make the frosting:

  • While rolls bake, beat cream cheese and butter until smooth. Add vanilla. Gradually beat in powdered sugar, cocoa, espresso powder, and a pinch of salt until combined. Slowly pour in the melted chocolate while mixing on low at the same time. Then add heavy cream 1 tbsp at a time and beat until desired spreading consistency is reached.

Frost and serve:

  • Remove rolls from oven and cool 5–10 minutes. Frost generously and enjoy warm.

Notes

If using active dry yeast then you need to activated the yeast first. Warm the buttermilk over low–medium heat until between 105–115°F. Pour into a small bowl and stir in yeast. Let sit ~10 minutes until foamy.