Cast Iron Chocolate Cinnamon Rolls

Last Updated on July 8, 2025 by DIYbunker Team

There’s something deeply satisfying about making chocolate cinnamon rolls from scratch, especially when they’re baked in a cast iron skillet for that perfect balance of soft, gooey centers and golden edges. This recipe starts with a pillowy, enriched dough that comes together in the stand mixer, rises until light, and is then rolled out and slathered with a rich chocolate filling made from butter, brown sugar, and cocoa.

After a second rise, a pour of heavy cream ensures the rolls stay moist as they bake, and a generous drizzle of caramel cream cheese frosting melts into every swirl. The result is a batch of chocolate cinnamon rolls that are as impressive to serve as they are comforting to eat—warm, decadent, and just a little bit indulgent.

Recipe Details

Yield: 8-12 rolls

Equipment:

• 10-12 inch Cast Iron Pan
• Rolling Pin
• Stand Mixer with Paddle and Hook Attachment
• Sharp Knife/Thread

Prep Time: 20 minutes

Bake Time: 22 minutes

Idle Time: 50 minutes

Ingredients

Dough:

• 1 cup milk, warm
• 2 ½ teaspoons active dry yeast
• 2 eggs
• ½ cup unsalted butter, softened
• ½ cup white granulated sugar
• 1 teaspoon salt
• 4 cups all purpose flour (extra ½ cup)

Filling:

• ½ cup unsalted butter, softened
• 1 cup brown sugar
• ½ cup cocoa powder
• ½ teaspoon vanilla extract
• ¼ cup heavy cream

Frosting:

• ⅓ cup butter, softened
• 4 ounces cream cheese
• ⅓ cup caramel sauce
• 1 tablespoon vanilla extract
• 2 cups powdered sugar

Directions

1. In a stand mixer bowl add the warm milk and yeast. Stir and let sit for a couple minutes to allow the yeast to activate.
2. Once the milk becomes a bit puffy from the activated yeast, add in the butter, eggs and white sugar. Use the paddle attachment to beat these ingredients together until combined.
3. Then add in the 4 cups of flour and salt. Beat together until the dry ingredients are JUST combined, then stop. Remove the paddle attachment and let the mixture sit for 5 minutes, allowing the flour to soak up the wet ingredients.
4. Then attach the dough hook and knead the dough for 5-7 minutes until it becomes slightly tacky. If the dough is too sticky, add in the xtra ½ cup of flour, adding only a tablespoon at a time until no more is needed.
5. Place a damp towel or plastic wrap over the dough and let rise at room temperature for 30 minutes. 
6. While the dough is rising, make the chocolate filling. In a medium bowl add the softened butter, cubed. Then add the sugar and cocoa powder. Blend together with a fork until incorporated and a thick paste is created. 
7. Add the vanilla extract, mixing once more until combined.
8. On a clean floured surface, place the risen dough and fold into a large rectangle about 9 inches by 13 inches and ½ inch thick.
9. Spread the chocolate filling into the dough slab evenly, covering every inch of the dough.
10. Roll the dough lengthwise into a tight log shape.
11. Use a very sharp knife or piece of string to cut 8-10 cinnamon rolls from the log. Each roll should be about 2 inches tall.
12. Place all the rolls in the cast iron pan, with a small amount of space surrounding them if possible. Cover these rolls and let them rise again for another 20 minutes or until they have doubled in size.
13. Preheat the oven to 375 degrees Fahrenheit.
14. Once they have proved for the second time, pour the heavy cream all over the tops of the rolls.
15. Bake in the oven for 24 minutes or until lightly golden brown and puffy.
16. While they are baking, make the caramel icing.
17. In a mixing bowl add the cream cheese and butter and whip with a hand mixer until smooth. Then pour in the caramel sauce and vanilla extract. Blend again until combined.
18. Lastly add the powdered sugar in 1 cup at a time, mixing in between until a thick glaze is formed. If it is too thick, add a tablespoon of milk to thin out to your desired consistency. (Remember the icing will melt over the hot cinnamon rolls as well)
19. When the cinnamon rolls are done, drizzle the glaze on all of these chocolate cinnamon rolls. Use a diagonally method if you want to still see those chocolate rolls under the icing.
20. Serve while warm and enjoy!

Notes:

• Make sure the milk is warm and not hot or it will kill the yeast and the dough won’t rise properly.
• Do not let the dough rise for too long in the initial rise or the cinnamon rolls will be too airy.

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