Cinnamon rolls are a must-have around the holidays. In fact, this recipe is so easy to make ahead and enjoy Christmas morning. The addition of chocolate and caramel have them doubling as a dessert, but the light and fluffy pastry make them perfect for breakfast or brunch.
There is little else I like better than cinnamon rolls. They’re ooey-gooey, melt in your mouth, and make lingering over breakfast a must. The only thing that could make them better is chocolate… and not having to make frosting!!
Now don’t get me wrong, I love frosting and I’ve been known to eat it with a spoon a time or two. Just a time or two.
There’s a beauty in simply dumping a pan upside down and watching lovely golden sticky caramel sauce drip out. And there’s a beauty in diving in face first and eating it too, but more so when no one else is there to witness your stickiness.
I’ve come to the determination that everything just looks better in a cast iron pan. Like makes me want to take a picture every time better, and no, not just because I happen to blog about scrumptious recipes. This recipe can be made in a 9×13 pan, but in true pioneer fashion (you did know this blog is based upon Pioneering Today, right?), you haven’t really cooked unless you bake your chocolate caramel cinnamon rolls in a cast iron skillet.
Why I Love This Recipe
- Who doesn’t love sweet, sticky and delicious cinnamon rolls? But incase you needed more reasons to love this recipe, here they are…
- You can make them from my artisan no-knead dough, which I oftentimes have sitting, ready to use in my refrigerator.
- You can follow the recipe as written below and get them just to the baking point, then let them sit overnight in the refrigerator for quick baking in the morning.
- No need to let the cinnamon rolls cool before frosting, the ooey-gooey caramel sauce acts like frosting and you can enjoy them hot out of the oven.
Cinnamon Roll Dough Instructions
- If you want to save time on this recipe, then use my no-knead artisan bread dough recipe and make it up to two weeks ahead of time. Then, just leave it in your refrigerator until ready to bake.
- If using the recipe below, pour warm water and milk over yeast in a glass, plastic, or wooden bowl. (Never use metal for bread. It doesn’t hold the heat and can cause it not to rise as well.) Let sit for 8 to 10 minutes until foamy.
- Add egg, butter, and sugar to the bowl and stir to combine.
- Stir in salt and flour. Knead for 6 to 8 minutes on a lightly floured surface. The dough should feel smooth, not sticky. If it’s sticky, keep adding small amounts of flour, 1 tablespoon at a time, until smooth.
- Cover dough with a tea towel (traps warmth and helps dough from forming a dry crust on top) and allow to rise for an hour in a draft-free spot. I always put mine on the top of the fridge or in your oven with just the oven light on works, too.
Preparing the Cinnamon Rolls
Cast Iron Skillet Directions:
- Measure out 1/2 cup of butter (or coconut oil for dairy-free) and divide it between the two pans, putting a little bit more oil in the larger pan. Place the skillets in the oven and hit pre-heat. As soon as the coconut melts completely, after about 3 to 5 minutes, turn off the oven. (Alternatively, you can melt your butter ahead of time and proceed with making the caramel in a cool cast iron skillet.)
- Using an oven mitt, because we don’t want to burn our fingers, pull out the skillets. Swirl the melted butter around until it covers the whole surface of the pan. Sprinkle the brown sugar and optional cocoa powder over the melted butter and set pans aside.
- Put your rolls, cut side down, into the skillet. The heat from the cast iron will help these rolls to rise nicely, especially on chilly fall and winter days, and because of the smaller pan, the rolls will puff up instead of out. (Anyone else’s favorite part the center of the cinnamon roll, especially when it’s almost not quite all the way done?)
9×13 Pan Directions:
- Layer ingredients for chocolate caramel sauce in your 9×13 pan.
- After dough has risen, roll out on a lightly floured surface into a rectangle approximately 18×14 inches. Spread softened butter over surface of dough.
- Sprinkle brown sugar, cocoa powder, cinnamon, and chocolate chips over the surface.
- Roll up, keeping it tight as you go (like rolling up a sleeping bag).
5. Cut into approximately 15 equal-sized pieces with a sharp knife. You can use thread or dental floss as well. I find quilting thread works better than regular thread as it’s thicker.
6. Place cut edge down in a pan on top of the sauce ingredients, with sides just touching.
7. Cover with tea towel and allow to rise for one hour. Or cover with plastic wrap and put in fridge if baking in the morning, allow to come to room temperature before baking.
- Preheat the oven to 375 degrees. Allow cinnamon rolls to come to room temperature if stored in the refrigerator overnight.
- Bake for 12 to 25 minutes, depending on how thick you cut them. I prefer mine on the doughier side so I pull them out as soon as they’re golden on top.
- Let cool in the pan for 3 minutes, then invert over platter or plate. Scrape remaining caramel sauce from pan onto cinnamon rolls. Enjoy!
Tips for This Recipe
- If you want to save time, make my no-knead artisan dough up to two weeks ahead of time. Then, use half the dough for this cinnamon roll recipe.
- Alternatively, you can prepare everything right up to the baking point, then cover and let them sit overnight in the refrigerator and bake in the morning. Then, allow them to preheat in the oven until 175 degrees, turn off the oven and check to see if they have doubled in size.
- Don’t let the cinnamon rolls cool completely in the pan, they’ll be very hard to turn out onto a pan and some of that delicious caramel will be left behind.
- For an extra chocolatey version, you can add the additional 1/4 cup of cocoa powder to both the filling and the caramel sauce.
- Try cutting your cinnamon rolls with thread for nice, even cuts.
More Breakfast & Bread Recipes
- Homemade Pop Tarts
- Sourdough Chocolate Quick Bread
- Fried Donuts from Scratch
- Homemade Pumpkin Roll
- Blueberry Pudding Recipe
- Jam Roly-Poly – Vintage Recipe from Great-Grandma
- Cranberry Muffin Recipe
- Blueberry Skillet Cake
- 1930s Chocolate Gravy Recipe
- EASIEST Homemade Bao Bun Recipe
Did you make this recipe? Snap a photo and tag me on social media, I’d LOVE to see your flaky pie crust! Then be sure to rate this recipe by clicking the stars in the recipe card below!
Old-Fashioned Homemade Chocolate Cinnamon Caramel Rolls
- 1/2 cups water warm, 120 degrees or lukewarm on your wrist
- 1/2 cup milk warm
- 2 1/4 tsp yeast
- 1 egg
- 1/2 cup butter softened
- 1/2 cup sugar
- 1 tsp salt
- 3 3/4 cups flour unsifted, all-purpose, pastry or bread flour (plus 1/2 cup or so for dusting your work surface)
- 1/2 cup butter melted (or coconut oil for dairy-free)
- 1/2 cup brown sugar
- 1/4 cup cocoa powder optional
Chocolate Cinnamon Filling
- 1/4 cup butter softened
- 1/2 cup brown sugar
- Cinnamon to taste
- 1/2 cup semi-sweet chocolate chips or raisins, nuts, or other dried fruit
- 1/4 cup cocoa powder optional
- Pour warm water and milk over yeast in a glass, plastic, or wooden bowl. (Never use metal for bread. It doesn't hold the heat and will kill your yeast.) Let sit for 8 to 10 minutes until foamy.
- Add egg, butter, and sugar to bowl and stir to combine. Stir
- Stir in salt and flour. Knead for 6 to 8 minutes on a lightly floured surface. Dough should feel smooth, not sticky. If it's sticky, keep adding small amounts of flour, 1 tablespoon at a time, until smooth.
- Cover dough with a tea towel (traps warmth and helps dough to rise) and allow to rise for an hour in a draft free spot. I always put mine on the top of the fridge or your oven with just the oven light on works, too.
- Layer ingredients for caramel sauce in your cast iron or 9×13 pan.
Chocolate Cinnamon Filling
- Once the dough has doubled in size (usually takes 45 to 60 minutes) roll out on a lightly floured surface into a rectangle approximately 18×14 inches. Spread softened butter over the surface of the dough. Sprinkle brown sugar, cinnamon, chocolate chips, and optional cocoa powder over the surface.
- Roll up, keeping it tight as you go. Cut into approximately 15 equal pieces. Place cut edge down in the pan on top of the sauce with sides just touching.
- Cover with tea towel and allow to rise for one hour. Or cover with plastic wrap and put in fridge if baking in the morning (allow to come to room temperature before baking).
- Bake at 375 degrees for 12 to 25 minutes, depending on how thick you cut them. I prefer mine on the doughier side so I pull them out as soon as they're golden on top.
- Let cool in pan for 3 minutes then invert over platter or plate. Scrape remaining caramel sauce from pan onto cinnamon rolls. Enjoy!
- For a make-ahead version, use my No-Knead Artisan Bread Dough, it can be made up to two weeks ahead of time and be ready and waiting in your refrigerator.
- In my husband’s opinion, it’s not dessert unless it’s chocolate. Add 1/4 cup cocoa powder to the pan with other glaze ingredients, and 1/4 cup cocoa powder sprinkled with the filling ingredients. You can omit the cinnamon if you wish, but chocolate and cinnamon do go well together.
This recipe was originally written in 2012, but has been updated with newer photos, a video and an updated version of the recipe.