I had planned to wait and share a different recipe right after sharing my challah bread recipe with all of you, but I am WAY too excited to postpone these challah cinnamon rolls! They take the exact same base dough as the bread and are rolled into the perfect, pillowy soft cinnamon rolls that melt in your mouth. Honestly, this cinnamon experiment was a total whim, but my love of sweets (and carbs) won out and here we are.

Why Challah Bread Cinnamon Rolls?
As I was experimenting with challah bread, I did a lot of tasting, and I realized that challah dough is nothing if not a lightly sweetened pastry dough! It would be perfect in a number of applications like this. Why go out of my way to try to create another sweet pastry dough when the ideal was already right at my fingertips? Er, rather, on my fingertips. Because my hands were covered in dough.
When I first dove into my challahventures, a dear friend sent me a link to this Instagram profile- Mandylicious: The Challah Guru. While her recipes are not vegan, I did not even know you could get this creative with challah bread! LOOK AT HER STUFF. THERE IS FUNFETTI CHALLAH. THERE IS CHALLAH MONKEY BREAD (and I am so figuring that out in the future!) So when I began to think about how I could get creative with this dough in my own kitchen, cinnamon rolls were the first thing to come to me. The first of what I hope are many more challah experiments.

How To Make The Cinnamon Rolls!
Firstly, make your dough. That recipe can be found here. After the initial two hour rest, instead of rolling your dough into ropes to bread a loaf of bread, roll it into a large, flat rectangle on either a lightly floured surface or a pastry mat. My pastry mat from Joseph Joseph is 14.5″ x 22″, so these are the dimensions I go for when rolling. The dough will come out fairly thin with a rectangle of this size.

Then, we mix and add our filling. My filling contains lightly softened coconut oil (I was actually out of vegan butter but was very pleased with how this turned out), brown sugar, and cinnamon. You really need to work it in with your fingers to spread it across the entire rectangle, leaving room around the edges for sealing the roll.

I did not get it pictured, because there was no decent way to fit it in the frame, but this is where you will take one of the naked ends of your dough, and fold the edge in on itself. Then you roll, and roll, and roll, ensuring your roll stays nice and tight. Once you’ve rolled up the entire rectangle, gently press the other naked edge edge into the dough roll so everything seals together nicely.
Then slice! I sliced my cinnamon rolls with a serrated to be about an inch tall. This makes smaller, bite-sized cinnamon rolls. But if you want the big ones (you know, the giant cinnamon rolls that you can bury your whole face in), cut them wider. I would suggest cutting them into 12 equal pieces to get fewer, larger cinnamon rolls. I cut these into 15 cinnamon rolls, and they were very tasty, but small!

Do not be fooled by the small, sixteenth roll. That’s just an end piece that very quickly wound up in my mouth. Fifteen rolls were placed into a parchment lined pyrex and left to rise for an additional two hours.
Yes, yes. I know. It’s a long time. But trust me. Just like with the traditional challah, these will get some INSANE volume with the extra rest. Do not be tempted to skimp out on the two hours.
Just before the rise is done, preheat your oven to 350 degrees.

If you’d like, you can brush these with the same glaze used on the challah bread before you put them in the oven. It is not required, but I love how golden the rolls become when I do it.
LIKE SO:

Top with a sweet vanilla glaze (I use a combination of powdered sugar, vanilla, and unsweetened, nondairy milk) and THERE YOU GO.
Challah Bread Cinnamon Rolls
Equipment
- 9"x13" glass baking dish (such as a Pyrex)
- Large pastry mat
- Parchment paper
- Rolling pin
Ingredients
- 1 recipe Vegan Challah Bread dough
For The Filling:
- ¼ cup REFINED coconut oil softened
- ½ cup brown sugar
- 1 ½ tablespoons cinnamon
For the 'Egg Wash:'
- 2 tablespoons nondairy milk unsweetened
- 1 tablespoon maple syrup
For the Vanilla Glaze:
- 1 cup powdered sugar
- 1 ½ tablespoons nondairy milk unsweetened
- ½ teaspoon vanilla extract
Instructions
- Prepare the vegan challah bread dough and allow to rise for two hours. The dough will not necessarily double in size after the first rise, and that is okay!
- When there is 10-15 minutes left on the rise, prepare your cinnamon roll filling. Mix the coconut oil, cinnamon, and brown sugar together in a bowl until well combined.
- Once the first rise is completely, roll the dough into a large, thin rectangle, approximately 14" x 22"
- Spread the cinnamon mixture over the dough, leaving a 1" border all the way around the dough. This will allow you to seal the edges of the cinnamon rolls once you form a log.
- Starting at the long edge, roll the dough rectangle into a tight log. Press the exterior, uncoated end of dough down to seal the roll.
- Slice the log into 12 to 15 rolls with a serrated blade, depending on how large or small you prefer your rolls to be. The cinnamon rolls pictured were sliced at 1 inch thickness, yielding 15 cinnamon rolls.
- Place the rolls in a 9×13 glass dish lined with parchment paper.
- Transfer the dish to a warm spot in your kitchen and leave to rise for an additional two hours. The rolls will expand significantly.
- Optional: brush the rolls with 'egg wash.'
- Bake for 18-20 minutes, or until the rolls are lightly golden.
- While the rolls are baking, prepare the vanilla glaze: whisk powdered sugar, nondairy milk, and vanilla extract together in a bowl until well combined.
- Allow the rolls to cool in the pan for fifteen minutes before drizzling with vanilla glaze.
- You can eat these immediately, or microwave individual rolls for 30 seconds each to reheat.
I’m feeling a little under the weather currently, and I cannot wait until I’m feeling up to making another batch of these. I have a funny feeling that when I do, they won’t last long.

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