Roasted Garlic, Peppers, & Cheese Stuffed Challah Bread

Alright, this has been something that I have been making for friends and family for a little while now and I think it is finally time for me to share it with you. The challah dough itself is a recipe I took from Adeena Sussman’s Sababa cookbook. It is perfection, so I do not stray from her dough recipe but I do play around a bit by stuffing the bread. 

Tool Kit:

For the Dough:

  • 7 cups of flour
  • ½ cup sugar
  • ⅓ cup olive oil
  • ⅓ cup honey
  • 5 teaspoons instant yeast
  • 3 eggs (2 go in the dough and 1 is for the eggwash)
  • 1 ¾ cup warm water
  • seasalt ( 1 tablespoon for the dough and about a teaspoon for the top of the bread)

For the Stuffed Portion

  • 3 large heads of garlic
  • 3-6 jalapenos depending on how spicy you are feeling today (or whatever pepper fits your spice preference serranos are also tasty in this)
  • Olive oil
  • Salt
  • Pepper
  • Your favorite cheddar (shredded)

A Few Notes

  • The amounts listed are for 3 large challah loaves 
  • You can always leave out the cheese to make it kosher if you’re serving meat with it or if you just are not in a cheesy mood today
  • I like to break this up into two days to allow the bread lots of time to relax in the fridge overnight
  • Time to create the dough: about 25mins
  • Total time (excluding the resting overnight): about 4 hours

Let’s Do This!!

DAY 1:

In the bowl of your stand mixer, fitted with the dough hook, put in the flour, salt, sugar, olive oil, honey, eggs, warm water, and yeast. Mix on low until the threat of flour getting everywhere is gone. Then increase the speed to medium and let it go until a ball of dough is formed.

Pull the dough out, knead it a few more times if you have some crumbly stragglers, and place it in a large oiled bowl. Make sure you get a bit of the oil all over the dough ball so it doesn’t get stuck to the sides of the bowl when rising.

Now cover the bowl with a clean kitchen towel and place it somewhere warm to rise for an hour.

After the first rise is complete, turn the dough out on a clean surface and divide the dough up into 3 even chunks. I find using a kitchen scale to be the easiest way to ensure they are three equal parts. Cover each piece up with plastic wrap or bee’s wrap and stick them in the fridge to rest overnight.

DAY 2:

Preheat your oven to 350F. Cut the tops off of all the garlic heads, place them each in their own foil purse and top them with olive oil, salt, & pepper. Get out a bake sheet lined with parchment paper or a silicon mat and place the foil purses and all the peppers onto the bake sheet. 

Let them hang out in the oven for 30-50 minutes, start checking on them around the 30 min mark, you want the peppers to look blistered and you want the garlic to look brown and mushy but not burnt. While you wait on items to finish roasting, now would be a great time to shred your cheese.

Pull them out of the oven and allow them to cool completely. 

Once cooled, Squeeze out all the garlic and lightly smash them with your knife until a paste forms. Peel all of the skin off of the peppers, discard the skin, and chop up the pepper seeds and all. 

Pull the dough out of the fridge and divide each into 3 smaller portions. Take them and roll them out into little snakes or ropes. Once you get them all to your desired length, flatten them out.  This is where you’ll brush on your garlic & peppers and then carefully place the cheese on top. Then roll them back up and be careful not to let the fillings ooze out in the process. Next is the easy part: the braiding. Squish the tops of 3 ropes together and braid them normally and tuck the ends under themselves. Repeat for all 3 loaves. Now you, and the bread, get to rest. Place them on a bake sheet lined with parchment paper or a silicone mat, cover them with a clean kitchen towel, and allow them to rise in a warm place for an hour.

Preheat your oven to 350F. While you wait for the oven, get started on the egg wash. All you need is one egg and a splash of water, mix it up and then brush it onto each loaf and then add your salt on top.

Place them in the oven for 25 minutes and allow them to cool slightly before serving.


Published by Self Taught Sloth

Hi, I'm April and I love to eat. LOVE IT. I base my whole day around what and when my next meal is going to be. I love creating different dishes, some of which are meh and others are crave-worthy. However, I grew up in a family of people who went out to eat every night. My mother hates the very idea of cooking and uses the oven as storage. I had this desire to create, cook, and bake, but I didn't know how. So I started researching by watching cooking shows and reading every cookbook I could get my hands on and taught myself how to create the types of dishes I wanted to try but didn't want to go out and pay for. Here you will find all my favorite things to create as well as a sprinkle of some travel content. I hope to inspire you all to get out there and create and have fun in your kitchen and to travel the world and just overall eat great food.

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