During the Jewish high holidays, the only thing that's better than challah  for dinner is challah for dessert! When it comes to constructing a sweet loaf, peanut butter and chocolate and cinnamon and sugar are two classic combinations that you can't go wrong with. These aren't, however, the type of fillings that should be blended into the challah dough: in cinnamon-roll-like fashion, here are step-by-step photos to help you fill your challah loaves with sugary swirls.
Follow the recipe for basic challah dough . For each filled loaf, you'll need four smaller pieces of dough. Roll out each piece of challah dough thinly, about 1/4-inch thick.
Peanut Butter and Chocolate Measurements
If you're following our basic challah recipe , then for the peanut butter and chocolate fillings, you will need about 1 cup of chocolate chips and four 1-1/2-ounce packages of peanut butter. If you have a large jar of peanut butter, use about 1-1/2 tablespoons per challah piece.
Spread the Peanut Butter
Spread the peanut butter with an offset palate knife. Leave about 1/2 inch of space around the rim of the challah dough.
Dot With Chocolate
Dot the challah with 1/4 cup of chocolate chips, and then roll it like a burrito.
Braiding this challah isn't quite as complicated as a six-strand rendition . Instead, take the four stuffed strands, and weave them under and over each other to create a hashtag with eight ends. Take the top two pieces of dough and twist them together. Follow the same pattern for the rest of the pieces, until there are four ends. Pinch two of the twisted ends together and repeat on the other side, so you are left with a long, twisted loaf. Then take the two ends of the loaf and pinch them together, so a circular shape is formed. Tuck the pinched end underneath the dough to prevent it from unraveling.
Peanut Butter and Chocolate Challah
Bake as your recipe directs . The egg wash  gives it a stunning yellow hue and shine.
Inside the Loaf
The peanut butter swirls and large chunks of chocolate are very visible!
Cinnamon Sugar Measurements
For cinnamon-sugar-filled challah, mix four tablespoons of granulated sugar with a dash or two of cinnamon.
Spread Cinnamon Sugar
Spread the sugar mixture carefully around a flattened piece of basic challah dough , but leave a border of space about 1/2 to 1 inch.
Roll it like a burrito, but carefully, so no sugar falls out. Pinch the ends as you roll to avoid spillage. If any sugar gets on the outside of the dough, the challah won't seal, and the bread will be a sticky, burnt sugary mess as it bakes!
Lift the End
Once you get to the end, lift the end up and pinch it to seal the burrito.
Seal the Strand
Be very sure to securely pinch all of the dough together, so none of the sugar falls out.
Cinnamon Sugar Challah
Braid the challah as directed before, and bake according to the recipe .
Inside the Challah
This challah is light, moist, and sweet with a faint hint of cinnamon.