Challah Cinnamon Rolls

So, you’ve got some glorious challah bread, maybe from Shabbat, maybe just because you love it, and now you’re looking at it thinking, “How can I make this even MORE indulgent?” Or perhaps, you’re just hankering for a cinnamon roll that hits different, something next-level fluffy and rich. Friend, you’ve come to the right place. We’re about to turn that beautiful braided loaf into the most epic Challah Cinnamon Rolls your tastebuds have ever encountered. Get ready to have your mind blown (and your kitchen smelling like pure heaven).

Why This Recipe is Awesome

Honestly, it’s like challah and a cinnamon roll had a delicious, fluffy, golden-brown baby, and let me tell you, this kid is a star. This recipe takes everything you love about the rich, slightly sweet, tender crumb of challah and marries it with the gooey, cinnamon-spiced perfection of a classic cinnamon roll. The result? Rolls that are ridiculously soft, ridiculously flavorful, and frankly, ridiculously easy to devour. Plus, it’s a fantastic way to use up leftover challah that might be on its last leg, or an excuse to make challah from scratch just for this purpose (no judgment here!). It’s practically idiot-proof, even I didn’t mess it up, and that’s saying something.

Ingredients You’ll Need

Okay, gather your troops! Most of these are pantry staples, so you probably won’t need to raid a specialty store. Unless your specialty store is your pantry. Which, same.

For the Challah Dough (or use 1 large, store-bought challah loaf if you’re skipping the homemade dough step):

• 1 cup warm water or milk (about 105-115°F/40-46°C – like a cozy bath for yeast, not a hot tub)
• 2 ¼ teaspoons active dry yeast (that’s one standard packet, folks!)
• ½ cup granulated sugar (for sweetness and to feed our tiny yeast friends)
• ½ cup vegetable oil (or olive oil, don’t overthink it)
• 2 large eggs + 1 egg yolk (for richness and that glorious golden hue)
• 1 teaspoon salt (flavor enhancer extraordinaire)
• 4-5 cups all-purpose flour (the main character, give or take a little)

For the Irresistible Cinnamon Filling:

• ½ cup unsalted butter (softened, like really soft, but NOT melted unless you’re a monster)
• 1 cup packed light or dark brown sugar (your call, both are delicious)
• 2 tablespoons ground cinnamon (don’t skimp, this is the star spice!)

For the Dreamy Cream Cheese Glaze:

• 4 oz cream cheese (softened, obviously, or it’ll be lumpy, and nobody wants lumpy glaze)
• 1 ½ – 2 cups powdered sugar (sifted if you’re fancy, otherwise YOLO)
• 2-3 tablespoons milk or cream (just a splash to get that perfect pourable consistency)
• 1 teaspoon vanilla extract (makes it sing!)

Step-by-Step Instructions

Alright, apron on, good vibes only! Let’s get these rolls rolling.

1. **If making challah dough from scratch:** In a large bowl, whisk together the warm water/milk, yeast, and a tablespoon of the sugar. Let it sit for 5-10 minutes until it gets foamy. That means your yeast is alive and ready to party!
2. Add the remaining sugar, oil, eggs, egg yolk, and salt to the foamy yeast mixture. Whisk well to combine.
3. Gradually add the flour, starting with 3 cups, mixing until a shaggy dough forms. Turn it out onto a lightly floured surface and knead for about 8-10 minutes until it’s smooth and elastic. It should spring back when poked. Add more flour sparingly if it’s too sticky.
4. Lightly grease a clean bowl, place the dough in it, and turn to coat. Cover with plastic wrap or a damp towel and let it rise in a warm place for 1-1.5 hours, or until doubled in size. This is your first rise – **patience is key!**
5. Once risen, gently punch down the dough to release the air. Turn it out onto a lightly floured surface.
6. **For the Filling:** In a small bowl, mix the brown sugar and cinnamon. Set aside.
7. Roll out your challah dough (or your store-bought challah, cut lengthwise and flattened a bit) into a large rectangle, about 12×18 inches and ¼ inch thick. Don’t go too thin!
8. Evenly spread the softened butter all over the dough, leaving a small border on one of the long edges. Then, sprinkle the brown sugar-cinnamon mixture generously over the butter, making sure to cover almost completely.
9. Starting from the long edge opposite the border, tightly roll the dough into a log. The tighter, the better for pretty spirals! Pinch the seam to seal it.
10. Using a sharp knife or unflavored dental floss (seriously, it works wonders!), cut the log into 12-15 equal slices, about 1-1.5 inches thick.
11. Arrange the rolls in a lightly greased 9×13 inch baking pan, leaving a little space between each roll as they’ll expand.
12. Cover the pan loosely with plastic wrap or a damp towel and let the rolls rise again in a warm place for 30-45 minutes, or until puffy and almost doubled. This is your second rise!
13. While they’re doing their thing, preheat your oven to 375°F (190°C).
14. Bake for 20-25 minutes, or until the rolls are golden brown and cooked through. **Keep an eye on them!**
15. **For the Glaze:** While the rolls are baking, whisk together the softened cream cheese, powdered sugar, milk/cream, and vanilla extract in a medium bowl until smooth and creamy. Add more milk if you want a thinner glaze.
16. Once the rolls come out of the oven, let them cool for just 5-10 minutes. Then, generously drizzle that glorious cream cheese glaze all over the warm rolls. The warmth helps the glaze melt perfectly into every nook and cranny.
17. Serve warm and bask in the glory of your culinary creation!

Common Mistakes to Avoid

Nobody’s perfect, but we can avoid some pitfalls, right? Learn from my past kitchen dramas.

• **Not activating your yeast properly:** If your yeast doesn’t get foamy, it’s probably dead. Don’t proceed with dead yeast; your rolls won’t rise, and that’s a sad day. Get new yeast.
• **Over-flouring the dough:** A little extra flour for kneading is fine, but don’t turn your beautiful challah dough into a dense brick. It should be soft and slightly tacky, not dry.
• **Melting the butter for the filling:** Softened, not liquid! If it’s melted, it will seep out when baking, leaving you with dry rolls and a messy pan. Nobody wants a butter escapee.
• **Not letting the dough rise enough:** This isn’t a race! Give the yeast time to do its job. Under-risen rolls will be dense and heavy.
• **Overbaking:** This is a big one. Keep an eye on those rolls! Once they’re golden brown, they’re likely done. Overbaked rolls will be dry and sad. **Nobody likes a dry cinnamon roll.**
• **Putting glaze on cold rolls:** Rookie mistake! The magic happens when the warm rolls meet the cool, creamy glaze. It melts slightly and coats everything perfectly.

Alternatives & Substitutions

Got a dietary restriction? Missing an ingredient? No stress, we can totally improvise!

• **No challah dough?** No problem! You can use a rich brioche dough, or even a good quality sweet milk bread dough. If you’re using store-bought challah, just slice it lengthwise and flatten it slightly before spreading the filling.
• **Dairy-free?** Swap butter for vegan butter sticks (like Miyoko’s or Earth Balance), milk for your favorite plant-based milk (almond, oat, soy), and use a vegan cream cheese alternative for the glaze.
• **Different spices?** Get wild! Add a pinch of cardamom, nutmeg, or even a touch of allspice to your cinnamon filling. Pumpkin spice blend would be amazing too.
• **Add-ins for the filling:** Want more texture or flavor? Sprinkle in some chopped pecans or walnuts, raisins, dried cranberries, or even some mini chocolate chips (my personal favorite way to elevate these, FYI).
• **Egg-free challah?** There are great vegan challah recipes out there that use flax eggs or applesauce. Just Google it!

FAQ (Frequently Asked Questions)

Got questions? I’ve got (casual) answers!

• **Can I make the challah dough ahead of time?** Absolutely! After the first rise, you can punch it down, put it in a greased bowl, cover it tightly, and refrigerate it for up to 24 hours. Just let it come to room temp for about 30-60 minutes before rolling it out.
• **How long do Challah Cinnamon Rolls keep?** They’re definitely best on day one, warm from the oven. But sealed in an airtight container at room temperature, they’ll be good for 2-3 days. Reheat gently in the microwave for a few seconds!
• **Can I freeze them?** Yes! Bake them, let them cool completely, and then freeze them unglazed in an airtight container for up to a month. Thaw them at room temperature, warm them up, and then apply fresh glaze. You can also freeze the unbaked rolls after the second rise.
• **Why challah specifically? Isn’t any dough fine?** Well, technically yes, but why settle for fine when you can have fantastic? The richness from the eggs and oil in challah dough gives these rolls an unparalleled tenderness and flavor that regular bread dough just can’t match. It’s next-level soft, IMO.
• **My rolls came out dry! What did I do wrong?** Likely culprits are overbaking (keep a closer eye on them next time!) or not letting the dough rise enough. Sometimes dough that’s too stiff from too much flour can also contribute.
• **Do I need a stand mixer to make the challah dough?** Nope! While a stand mixer with a dough hook makes life easier, you can totally knead the dough by hand. It’s a great arm workout and very therapeutic!
• **Can I skip the cream cheese glaze?** You *can*, but why would you want to hurt your soul like that? If you absolutely must, a simple powdered sugar glaze (powdered sugar + milk) or just a dusting of powdered sugar would work. But the cream cheese glaze is peak deliciousness.

Final Thoughts

And there you have it! You’ve just created a batch of Challah Cinnamon Rolls that are so good, they might just become your new signature bake. Whether you’re making them for brunch, a special treat, or just because it’s Tuesday and you deserve it, these rolls are a guaranteed mood booster. Now go forth and impress someone—or more importantly, yourself—with your new culinary skills. You’ve earned every fluffy, gooey bite!