In the bowl of the mixer, add the yeast, 1 tablespoon of sugar and warm water. Mix lightly and cover with a dish towel for 10 minutes for yeast to activate 

Add the sugar, egg, oil, flour, and salt and mix using your dough hook on medium speed until the dough comes together. If dough is too liquid or too sticky, add more flour, 1 tablespoon at a time

When dough comes together and is soft and elastic, remove from mixer and place in a greased bowl. Cover with a dish towel and let it rise for 90 minutes(or until doubled its size) in a warm area

In a bowl, combine the water, oil, and cocoa powder and confectioners sugar. Whisk until combined. 

Divide the dough into 6 equal portions and shape into balls. Cover with a dish towel 

Take one ball and roll into a narrow rectangle. Using a spoon or brush, add some of the liquid filling in the to the rectangle leaving a small border, then sprinkle the chocolate chips on top 

Roll this strip into a log (it will be a bit messy),  and repeat this step with the other 5 dough balls 

Place 6 dough strips side by side, and using your fingers, unite the tops. Braid 

Place challah in a cookie tin lined with parchment paper and let the dough rest for 90 minutes 

Preheat oven to 350 degrees Fahrenheit

Brush the top of the challah with the beaten egg. If you'd like, add some chocolate chips in the nooks and crannies 

Bake for 35-45 minutes or until the top of has browned 

Remove from the oven and place on a rack until completely cooled 

Enjoy!