Where do I begin… the quickest way to my heart is with a cinnamon roll. Some of my fondest memories as a child, teen, young adult and now even a so-called “adult” are those mornings with fresh cinnamon rolls. There is nothing like something warm and gooey to start off your day.

Now, if you add chocolate I won’t even be able to contain myself. It really doesn’t matter, give me the ones in a can, from a bakery, homemade, with cream cheese frosting, lemon frosting, maple frosting, even with no frosting at all and I am all yours! 

These sinfully large rolls are made with cocoa powder, cinnamon, and tons of butter and sugar. I sprinkled about 1/4 cup of mini chocolate morsels before rolling up the dough. BUT you can definitely take your liberties with other ingredients you roll up in these babies…  walnuts, raisins, or even crystallized ginger would all be amazing.

Technical Tip

When cutting your rolls you can use a couple different methods. You can use a serrated knife, pastry cutter, or even a length of dental floss to cut the dough into even-sized pieces. Ari and I are at odds on what way is best here. I prefer using floss, while she likes the serrated knife. Whatever way you choose, just make sure you use a sawing motion with a knife, so that you don’t squish the rolls. You also might want to discard the very ends of the roll since they often contain little filling.

I don’t believe that there is a better way than to spend a weekend morning with the smell of fresh chocolate cinnamon rolls coming out of the kitchen. We hope you enjoy these as much as we did!

Chocolate Cinnamon Rolls
Prep time: 
Cook time: 
Total time: 
Yields: 12
  • Dough:
  • 2¼ teaspoons active dry yeast
  • 1 cup water, warm
  • ½ cup granulated sugar
  • ¼ cup buttermilk
  • 1 tablespoon vanilla extract
  • 2 eggs, room temperature
  • 6 tablespoons butter melted and cooled
  • 5 - 5½ cups all-purpose flour
  • 2 teaspoons salt
  • Chocolate Cinnamon Filling:
  • 3 tablespoons unsweetened cocoa powder
  • 2 teaspoons cinnamon
  • 1½ cups of brown sugar
  • 1 teaspoon cornstarch
  • 1 stick of very soft butter
  1. In the bowl of a stand mixer fitted with a dough hook; add water, sugar and yeast. Swirl to combine. Allow yeast to bloom, about 5-7 minutes.
  2. In the meantime: Combine buttermilk, eggs, vanilla, salt, and melted-cooled-butter. Beat with a fork until eggs are mixed in.
  3. Once yeast mixture is bubbly and frothy, add buttermilk-egg mixture to bowl of stand mixer. Mix on low and add 4 cups of flour, one cup at a time. Once flour is mixed in, slowly add remaining flour slowly until dough becomes a ball and completely pulls away from the walls of the mixer. Your dough ball will clean the bowl. Remove from mixing bowl and knead dough on lightly floured surface about 8 times to form a ball. The dough should not stick to your fingers.
  4. Add 1 teaspoon of melted butter to a medium-large bowl. Place dough into the bowl and then flip the dough over to cover with the butter. Cover loosely with plastic wrap and drape bowl with a towel. Set the bowl in a warm place in your kitchen. Allow dough to rise for 60-90 minutes until doubled in size.
  5. While the dough is rising, combine brown sugar, cocoa powder, cinnamon and cornstarch in a medium bowl. Stir with as fork until combined. Set aside.
  6. Generously butter a 9x13” baking pan.
  7. Once dough has doubled in size, turn dough out onto a lightly floured surface. (Tip: if your dough is on the dry side rub your hands and counter with a little olive oil instead of flour. This will add some needed moisture to the dough). Knead the dough a few turns, then using a rolling pin, roll out an 18"x24" wide rectangle.
  8. Spread the stick of softened butter around dough, making sure to leave ½ - 1 inch around the sides.
  9. Sprinkle brown sugar-cocoa filling mixture over the butter. Tightly roll the dough from the shorter side or longer side and pinch the ends together to stop the filling from spilling out.
  10. Cut dough roll in half and then cut those halves in half, giving you 4 pieces. Cut each of those pieces into ⅓rd. This will give you 12 pieces.
  11. Place pieces in buttered baking pan.
  12. Place pan with rolls in a warm place for 1-2 hour or until nearly double in size.
  13. Preheat your oven and bake at 350°F for 20-30 minutes, rotating the pans every ten minutes. Rolls will be a light golden brown.
If you would like to split up your time you can chill your sliced rolls before baking. After step 11, cover with saran wrap and put in the refrigerator, and chill over night or for up to 16 hours. When you are ready to bake the rolls, place a boiling pot of water on the bottom shelf of a cold oven and the rolls on the top shelf. Don't forget to remove the saran wrap. Leave in the closed oven to proof for 30 min. After 30 min, remove the pot of water and rolls from the oven, and preheat to 350°F and bake as directed above.