Chocolate Cinnamon Challah

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I get all jittery and excited when attempting something new, although instinct forces me to revert to the safety net, a quantum of familiarity. Challah was one of those ideas which I wrestled with in my head. I wanted to feel good about turning it into something like french toast/ some flavoured version/lay on the stuffing options, please, that kind of thing. I came across a recipe for double chocolate chip challah quite a while ago but stuffed it in the back of my mental archives; I’m always timid when it comes to doing something old and traditional justice. The first attempt yielded too dry a texture (second photo below), though the taste and crumb itself wasn’t too far off the mark because the cocoa and decent amount of sugar incorporated into the batter made it more flavourful than expected. One does love surprises. So I adjusted the oil quantity to bump up the moisture, took it easy on the flour.

If you wish, you can attempt a chocolate gradient version– to each of the sections in the braid, you can add different quantities of cocoa, then adjust the remaining flour quantity from there. Who wouldn’t hit that stuff with a good knob of butter and honey? Please tell me, do.


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Chocolate Cinnamon Challah (makes one large or 2 small loaves)

600g all-purpose flour

12.5g active dry yeast (1.5 tbsp)

300ml warm water

1 tsp white sugar

35g cocoa powder (Hershey’s Special Dark works wonderfully here)

2 eggs

170g sugar

1 tsp salt

1 tbsp cinnamon

2 tsp vanilla extract

65ml vegetable oil

1 egg (for the egg wash)

pearl sugar (for sprinkling before baking)

In a small bowl, mix together the yeast, sugar and water. Wait 6-10 minutes for the yeast to activate, forming a thick layer of light brown foam on top.

Weigh out the flour and cocoa and put the two in separate bowls. In a large mixing bowl, whisk together 200g of the flour (a little more than 1.5 cups), the salt, sugar and cinnamon. Once the yeast has foamed up, add it to the flour mix and stir in briefly using a wooden spoon. Then, mix in the vanilla extract, eggs and vegetable oil. Add 125g of the remaining flour and stir into the dough. If using a mixer, switch to the dough hook attachment, but otherwise make like Simpleton Alex and use a wooden spoon or your hands to incorporate the flour. At this point, the dough will still be a little wet and shaggy. Almost limp.

Take the dough and roughly divide it into three. I just used my hands and eyes to guesstimate here. If you’re feeling very scientific, you may use a weighing scale for precision. Put each dough third into separate medium bowls (re-use your mixing bowl for one of them). To one of the dough thirds, add half the cocoa powder, a tablespoon at a time, and 60g of flour, give or take. I needed 60g but you might need a little more of less. I say a tablespoon at a time because it really depends how dark you wish to go with your bread. Do the same for another third. To the remaining third of dough, add the rest of the flour, though you might not need all of it. All thirds should have a similar texture after kneading for around 5-10 minutes– smooth, elastic, with a little bounce when you press its surface. Let the dough thirds rise in their individual bowls (greased first) for 2-3 hours.

Preheat the oven to 177C (350F). Remove the dough thirds, which should have at least doubled in size, from the bowls and place them on your work surface. Roll each to at least 12 inches or more in length. If you’re making 2 smaller loaves, divide each in half first before braiding. Press the tops together and start braiding like how you would do with your hair. Left over middle, right over middle, you get the gist. Once you reach the tails, brush the loaf (or loaves) with one beaten egg, and sprinkle with pearl sugar. Let rise for an hour, before baking in the preheated oven. The challah should feel fluffy to the touch, still retaining that bounce. Bake for 25-30 minutes. I took mine out at 17 minutes and it was perfect by then. The top of the chocolate part should be dark and shiny, and the plain part of the braid will be golden-brown. Mmm.

Freeze this loaf and slice whenever you want. It reheats wonderfully in the microwave! 20 seconds straight out the freezer to return to room temperature, then toast for maximum pleasure. Butter and jam/honey. Life is sweet like chocolate and cinnamon.

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